Tag: M.W=200-300

Electric Literature of 24393-53-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 24393-53-1 name is (E)-Ethyl 3-(4-bromophenyl)acrylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A method for constructing a quaternary carbon ring by visible light catalysis [2+2] reaction, comprising the following steps: The ruthenium complex 1 is used as a visible light catalyst, and 1.3 mg of the catalyst is added to 2 mL of 1,2-dichloroethane.0.2 mmol of (E)-ethyl-3-p-bromophenyl acrylate (corresponding R2 is p-bromophenyl, R3 is ethoxy), 1.0 mmol of 1,1-diphenylethylene (corresponding R1 is benzene) The base, R2 is a phenyl group) wherein the concentration of the visible light catalyst is 1.0 x 10-3 M. Pass argon for ten minutes,Then, with 450 nm ± 10 nm Blue LEDs, the light was illuminated in an argon atmosphere at 25 C for 5 h.After the reaction is completed, it is directly dried and separated by a column. Nuclear magnetic resonance spectrum, carbon spectrum,Mass spectrometryThe compound is a racemic ethyl-(2R)-2-(p-bromophenyl)-3,3-diphenyl-cyclobutyl-1-carboxylate.The conversion of the starting material was 100% and the yield of the cyclobutane product was 85%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (E)-Ethyl 3-(4-bromophenyl)acrylate, and friends who are interested can also refer to it.

Reference:
Patent; Chinese Academy Of Sciences Physics And Chemistry Technology Institute; Wu Lizhu; Lei Tao; Zhao Leimin; Zhou Chao; Liu Zan; Tong Zhenhe; (89 pag.)CN108623425; (2018); A;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 19376-57-9, name is Methyl 4,4,4-trichlorobutanoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 19376-57-9

To a stirred solution of methyl 4,4,4-trichlorobutanoate 2 (1.35 g, 6.57 mmol) in DCM (30 mL) at -78 C was added DIBAL-H (6.57 mL, 6.57 mmol, 1.0 M in hexanes) at a rate of 1.0 mL/min. The reaction mixture was stirred at -78 C for 1 h. After successive addition of MeOH (7 mL), HC1 (25 mL, 1 M) and Rochelle salt solution (25 mL, 1 M), the reaction mixture was stirred at room temperature for another 1 h. The separated organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by silica gel flash chromatography eluting with hexanes/EtOAc (20:1) to afford 4,4,4-trichlorobutanal 3 (1.15 g, 5.78 mmol) as a colourless oil in a yield of 88 %. ?H NMR (400 MHz, CDC13) S9.85 (br. s., 1H), 3.03-3.11 (m, 2H), 2.96-3.02 (m, 2H); ?3CNMR(100 MHz, CDC13) S 198.5, 98.9, 47.5, 41.2.

According to the analysis of related databases, 19376-57-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRITISH COLUMBIA CANCER AGENCY BRANCH; THE UNIVERSITY OF BRITISH COLUMBIA; YAN, Luping; ANDERSEN, Raymond, J.; SADAR, Marianne, Dorothy; MAWJI, Nasrin, R.; BANUELOS, Carmen, Adriana; WO2015/184393; (2015); A1;,
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Application of 1070-64-0,Some common heterocyclic compound, 1070-64-0, name is Ethyl 6,8-dichlorooctanoate, molecular formula is C10H18Cl2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

600 kg (2.48 kmol) racemic 6,8-dichloroethyl caprylate and 78 kg (2.43 kmol, 0.98 equiv.) sulphur in 576 kg ethanol were placed in a 6 m3 reactor with stirrer, metering pump, pressure and internal temperature measurement and also jacket heating. At an internal temperature of 110 C. and a pressure of 0.35 MPa, 2062 kg of an aqueous sodium sulphide solution (12.3 wt. %) comprising 253.6 kg Na2S (3.24 kmol, 1.31 equiv.) was metered in uniformly with stirring over a period of 85 min. The reaction mixture was stirred for another 120 min at 110 C. Then 508 g of a solution of sodium borohydride (12 wt. %) in sodium hydroxide solution (40 wt. %) comprising 61.0 kg NaBH4 (1.61 kmol, 0.65 equiv.) was metered in uniformly within 90 min. at 70 C. The ethanol contained was distilled off from the reaction mixture to the greatest possible extent, and thereupon a further 253 kg of a solution of sodium borohydride (12 wt. %) in sodium hydroxide solution (40 wt. %) comprising 30.4 kg NaBH4 (0.80 kmol, 0.32 equiv.) added over a period of 60 min. at 70 C. Once addition had taken place, the mixture was heated to boiling and stirred further for 30 min. at this temperature. After cooling, 540 kg MTBE was added and the batch was acidified to a pH value of 2.6 to 3.0 by adding 1454 kg (12.3 kmol) hydrochloric acid (31 wt. %). The organic phase was separated off and the organic solvent was distilled off completely without a vacuum. 506 kg of a yellow liquid was obtained, with a content of 94.0 wt. % dihydrolipoic acid and a polymer content of 5.6 wt. % (corresponds to a yield of 91.8% of theory).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 6,8-dichlorooctanoate, its application will become more common.

Reference:
Patent; ALZCHEM TROSTBERG GMBH; SCHNAPPERELLE, Ingo; WINKLER, Stephan; SANS, Juergen; THALHAMMER, Franz; (7 pag.)US2019/276396; (2019); A1;,
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Related Products of 6836-21-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 6836-21-1 name is Ethyl 2-(7-methoxynaphthalen-1-yl)acetate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

150 ml of ethanol is loaded into a three-necked reaction flask, magnetically stirred and equipped with a temperature probe, and cooled to 5C. When the temperature of 5C has been reached, 11.3 g of powdered calcium chloride(0.102 mol) is added, followed by 8.2 g of sodium borohydride (0.217 moles). After a few minute stirring at 5C, 10 g of 2-(7-methoxynaphthalen-1-yl)acetic acid ethyl ester 4 (41 mmols), dissolved in 100 ml of anhydrous THF, is added, the temperature being maintained under 10C. At the end of the addition the temperature is increased to room temperature and maintained at that temperature for about 2 hours. 5 ml of water is added slowly at the end of the reaction. 40 ml oftoluene and 20 ml of 30% HCl are then added. The phases are separated by re-extracting the aqueous phase with 20ml of toluene. The combined organic phases are washed with 40 ml of water, and then concentrated under vacuum to dryness to obtain 8.0 g of 2-(7-methoxynaphthalen-1-yl)ethanol 12. Yield 97%. The intermediate obtained was identifiedby NMR analysis: 1H NMR (400 MHz, DMSO-d6) delta 7.83 (d, 2H), 7.70 (m, 1H), 7.36 (m, 2H), 7.27 (m, 1H), 7.18 (m, 1H),3.92 (s, 3H), 3.75 (t, 2H), 3.29 (s, 1H), 3.19 (m, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-(7-methoxynaphthalen-1-yl)acetate, and friends who are interested can also refer to it.

Reference:
Patent; Procos S.p.A.; Barozza, Alessandro; Veronese, Martino; Roletto, Jacopo; Paissoni, Paolo; EP2703383; (2014); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 251085-87-7, name is Methyl 5-bromo-2-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of Methyl 5-bromo-2-chlorobenzoate

5-Bromo-2-chlorobenzaldehyde (74c). A solution of pyrrolidine (4.00 g, 56.0 mmol) in MTBE (12 mL) was added dropwise over 20 min to a solution of Red-Al (3.4 M solution in toluene, 16 ml, 54.4 mmol) in MTBE (33 mL) maintained at -20 C. The mixture was stirred for 1 h at 25 C. A solution of potassium tert-butoxide (0.60 g, 5.36 mmol) in THF (3 mL) was added. The resulting solution was added dropwise to a solution of 2-chloro-5-bromobenzoic acid methyl ester (72, 6.80 g, 27.3 mmol) in MTBE (15 mL) at 10 C. After 15 min the mixture was quenched with 2 N HCl (300 mL). Repeated recystallizations (hexanes) of the recovered material gave a crude solid (3.22 g, 54%, mp 43-46 C), which was used without further purification in the next step.; The synthesis of benzaldehyde chlorooxime synthons 52 is depicted in Scheme 4, below. Of the eight aldehydes 44e-f and 74a-f, only 44e and 74d were commercially available. The preparation of aldehyde 44f began with the known three-step transformation of 4-methyl-3-nitrobenzonitrile 63 to methoxy compound 64. See Reiner, J. E., et al., Bioorg. Med. Chem. Lett., 12, 1203-1208 (2002). alpha-Bromination of 64 using one equivalent of N-bromosuccinimide gave little selectivity between the mono- and dibromo adducts, but the analogous reaction using 2.5 equivalents gave dibromide 65 almost exclusively. Silver nitrate oxidation of dibromide 65 gave aldehyde 44f. See Hill. R. A., et al., J. Chem. Soc., Perkin Trans., 1, 2209-2215 (1987). The reaction of the o-nitrotoluene 63 with N,N-dimethylformamide dimethyl acetal in DMF gave the enamine 66, which underwent oxidative cleavage using sodium periodate in THF, see Riesgo, E. C., et al., J. Org. Chem., 61, 3017-3022 (1996), to give aldehyde 74a via a more facile preparation than previously reported. See Dann, O., et al., Liebigs Ann. Chem., 3, 409-425 (1984). Aldehyde 74b also has been prepared previously. See Schultz, E. M., et al., J. Med. Chem., 19(6), 783-787 (1976). A more expedient preparation of 74b began with chlorotoluene 67 undergoing alpha-bromination to 68, see Gilbert, A. M., et al., J. Med. Chem., 43, 1203-1214 (2000), by a modification of the original procedure. See Liu, P., et al., Synthesis, 14, 2078-2080 (2001). The reaction of 68 with 2-nitropropane and sodium ethoxide in ethanol gave 74b. See Mallory, F. M., et al., Tetrahedron, 57, 3715-3724 (2001). Commercially available aldehyde 69 and aldehyde 71, see Hino, K., et al., Chem. Pharm. Bull., 36(6), 3462-3467 (1988), which had been prepared via a Sandmeyer reaction from commercially available 70, were converted to methyl esters 72 and 73, respectively. The esters were converted to aldehydes 74c and 74e, respectively, using Red-Al(sodium bis(2-methoxyethoxy)aluminium hydride) (Aldrich Chemical Co., Inc., Milwaukee, Wisconsin, United States of America), pyrrolidine, and potassium tert-butoxide in methyl tert-butyl ether. See Abe, T., et al., Tetrahedron, 57, 2701-2710 (2001). Cyanoaldehyde 74f was prepared by debromocyanation of 44d. See Laali, K. K., et al., J. Org. Chem., 58, 1385-1392 (1993). Aldehydes 44e-44f and 74a-74f were converted to oxime derivatives 75a-h (of which 75a,e were known previously), see Quan, M. L., et al., J. Med. Chem., 42(15), 2752-2759 (1999), using hydroxylamine hydrochloride in either water/ethanol or pyridine/ethanol. The oximes were treated with N-chlorosuccinimide in DMF to give chlorooximes 52a-h, following the procedure reported for 52e. See Liu. K.-C., et al., J. Org. Chem., 45, 3916-3918 (1980). The chlorooximes 52 were reacted with acetylenes 51 without further purification.; Reagents and conditions: (a) H2, 10% Pd/C, EtOH; (b) NaNO2, aq. H2SO4; (c) CH3l, NaH, DMF; (d) NBS, benzoyl peroxide, CCl4; (e) AgNO3, aq. EtOH; (f) DMFDMA, DMF; (g) NalO4; aq. THF; (h) diethyl phosphite, (i-Pr)2NEt, THF; (j) 2-nitropropane, NaOEt, EtOH; (k) NaNO2, aq. HCl, then CuCN, KCN; (I) MeOH, H2SO4; (m) DCC, DMAP, MeOH, CH2Cl2; (n) Red-Al, t-BuOK, pyrrolidine, MTBE; (o) NH2OH HCl, H2O/EtOH or Py/EtOH (p) NCS, DMF.

The synthetic route of 251085-87-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; EP1719767; (2006); A1;,
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These common heterocyclic compound, 63243-76-5, name is Ethyl 2-amino-5-bromobenzoate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. HPLC of Formula: C9H10BrNO2

[00384] The mixture of 2-amino-5-bromo-benzoic acid ethyl ester (3.0 g, 13.16 mmol) and (0979) cyclopropanecarbonitrile (2.6 g, 39.47 mmol) in 6 M HCl/dioxane (60 mL) was stirred at reflux overnight. The solid was filtered, dried in vacuum to give 6-bromo-2-cyclopropyl-quinazolin-4-ol (3.3 g, yield: 95%) as crude product. MS: m/z 249.1 (M+H+).

The synthetic route of Ethyl 2-amino-5-bromobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HEDRICK Michael P.; HERSHBERGER Paul M.; MALONEY Patrick R.; PEDDIBHOTLA Satyamaheshwar; PINKERTON Anthony B.; WO2015/200534; A2; (2015);,
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Application of 167760-75-0,Some common heterocyclic compound, 167760-75-0, name is Methyl 4-amino-3-(trifluoromethyl)benzoate, molecular formula is C9H8F3NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Sodium nitrite (1.21 g, 0.017 mmol) was added to tetrafluoro boric acid (20 mL) in lot wise manner at -10C. The solution was stirred for 1 h at same tempreture then added methyl 4- amino-3-(trifluoromethyl)benzoate (3.5 g, 0.0 15 mmol) and continued stirring for h at sametempreture followed by addition of solution of KI (3.18 g, 0.0 19 mmol) in acetone : water (40 mL:60 mL).The reaction mass was stirred at rt for 1 h. The reaction mass was diluted with water and filtered to afford 4.8 g of title compound. ?H NMR (300 MHz, CDC13): 8.28 (s, 1H), 8.15-8.12 (d, J= 8.1Hz, 1H), 7.84-7.81 (d, J= 8.1Hz, 1H), 3.95(s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-amino-3-(trifluoromethyl)benzoate, its application will become more common.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; MUTHUKAMAN, Nagarajan; PISAL, Dnyandeo; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; KADAM, Sheetal R; (303 pag.)WO2016/55947; (2016); A1;,
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These common heterocyclic compound, 57486-69-8, name is Methyl 2-(2-bromophenyl)acetate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of Methyl 2-(2-bromophenyl)acetate

General procedure: In a three neck round bottom flask, CaCl2 (1.12 g, 10.2 mmol) was dissolved in ethanol (50 mL) under argon atmosphere. The resulting solution was cooled to 0 ?C, followed by the addition of NaBH4 (0.19 g, 5.1 mmol) at the same temperature. The resulting suspension was allowed to stir at 0 ?C for 30 min, after which a solution of S5a (1.0 g, 3.4 mmol) in 60 mL of Ethanol was added at the same temperature. The resulting reaction mixture was allowed to stir at 0 ?C for another 30 min, and then at rt for 15 h. After 15 h, 50 mL of a mixture of water and dichloromethane (1:1) was added to the reaction mixture which was then sonicated for 1 h. The resulting mixture was then subjected to vacuumfiltration over celite. The filtrate was collected and evaporated under reduced pressure. 50 mL of water was added to the resulting crude, which was then extracted with three portions of dichloromethane (30 mL each). The combined organic layer was dried over Na2SO4, and evaporated under reduced pressure to afford S6 2-(2-bromo-4,5-dimethoxyphenyl)ethanol (S6a): Brown Oil; (2.56 g, 60 %). 2-(2-bromo-5-methoxyphenyl)ethanol (S6b): Clear Oil; (1.29 g, 42 %). 2-(2-bromo-4-methoxyphenyl)ethanol (S6c): Clear Oil; (1.03 g, 55 %). 2-(2-bromophenyl)ethanol (S6d): Clear Oil; (2.41 g, 55 %).

The synthetic route of Methyl 2-(2-bromophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kapadia, Nirav; Harding, Wayne; Tetrahedron; vol. 69; 42; (2013); p. 8914 – 8920;,
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Reference of 87808-49-9,Some common heterocyclic compound, 87808-49-9, name is Methyl 2-bromo-4-methylbenzoate, molecular formula is C9H9BrO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

3-Bromo-4-methoxycarbonylbenzoic acid[0095] 2-bromo-4-methylbenzoic acid methyl ester (10.00 g, 42.8 mmol), tetrabutyl ammonium bromide (345 mg, 0.86 mmol), ruthenium chloride trihydrate (86 mg, 0.43 mmol), dichloroethane (14 mL) and sodium hypochlorite 10% (115 mL) were mixed. The pH at the aqueous phase was adjusted to 9.0 by addition of 20% v/v H2SO4. The biphasic mixture was stirred for 2.5 hours, and meanwhile, NaOH 20% v/v was added to keep the pH at 9. The phases were separated and the aqueous phase was washed with DCM (3 × 50 mL), acidified with 20% H2SO4 and extracted with EtOAc (3 × 50 mL). The organic layer was washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered and evaporated to dryness in vacuo to afford 3-bromo-4-methoxycarbonylbenzoic acid as a whitish solid (2.33 g, 21% yield). 1H-NMR (400 MHz, CDCl3): 8.38 (d, J = 1.5, 1H), 8.07 (dd, J = 8.1, 1.6, 1H), 7.84 (d, J = 8.1, 1H), 3.98 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-bromo-4-methylbenzoate, its application will become more common.

Reference:
Patent; Prous Institute for Biomedical Research, S.A.; Prous, Josep R.; Serradell, Neus; Munoz, Rosa; Flores, Ramon; Garcia-Delgado, Noemi; EP2573088; (2013); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 63746-12-3, name is Dimethyl 4-aminoisophthalate, A new synthetic method of this compound is introduced below., Quality Control of Dimethyl 4-aminoisophthalate

To a mixture of (4-adamantan-1-yl-phenoxy)-acetic acid (229 mg, 0.8 mmol) and 4-aminoisophthalic acid dimethyl ester (301 mg, 1.4 mmol) were dissolved in DMF (5 mL), and EDCHCl (140 mg, 0.75 mmol), HOAt (163 mg, 1.2 mmol) and DIPEA (0.21 ml, 1.2 mmol) was added. The mixture was stirred overnight, and then partitioned between ethyl acetate and brine. The organic phase was dried (MgSO4 anh), and concentrated. The residue was purified by silica gel column chromatography (CH2Cl2:MeOH=50:1) to give 4-[2-(4-Adamantan-1-yl-phenoxy)acetyl-amino]-isophthalic acid dimethyl ester as a white solid (281 mg, 76.3% yield). 1H-NMR (CDCl3, 300 Hz) 12.00 (1H, s, NH), 9.40 (1H, d, J=1.8 Hz, aromatic), 8.12 (1H, d, J=7.8 Hz, aromatic), 7.78 (1H, dd, J=8.1 & 1.8 Hz, aromatic), 7.33 (2H, m, aromatic), 7.03 (2H, m, aromatic), 4.65 (2H, s, OCH2CO), 3.97 (3H, s, OCH3), 3.95 (3H, s, OCH3), 2.09 (3H, m, adamantyl), 1.89-1.90 (6H, m, adamantyl), 1.72-1.82 (6H, m, adamantyl).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; US2009/306078; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics