Tag: M.W=200-300

These common heterocyclic compound, 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, 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. COA of Formula: C7H13BrO2

General procedure: Benzenesulfonamide (1.2mmol), ethyl alpha-bromophenylacetate or ethyl pheny-lacetate (2.4mmol), and toluene (4mL)werecombinedinasealedtubeequippedwith astirbar.Themixturewasstirredat50Cfor10min,TiCl4 (1.8 mmol) was added, andthereactionmixturewasheatedto115C.Afteravariableperiodoftimethe mixturewasdilutedwithH2O (10mL)toremovetheexcessofTiCl4, filtered,andextracted withAcOEt(3×15mL). The combined organic layers were dried over anhydrous Na2SO4 and thesolventwasevaporatedinvacuo.Crudecompoundswere purified by flash column chromatography (silicagel;cyclohexane=AcOEt 8:2). 2-Bromo-3-methyl-N-[(4-methylphenyl)sulfonyl]butanamide (4b). Orange oil, 57% yield; IR(KBr) 3528, 3235, 2970, 2880, 1718, 1597, 1450, 1171, 1085, 865, 550 cm-1; 1H NMR (CDCl3) d0.94 (d, 3H, J 6.6 Hz, CH3), 0.96 (d, 3H, J 6.6 Hz, CH3), 2.21 (octuplet, 1H, CH3CHCH3), 2.44 (s,3H, CH3Ph), 4.08 (d, 1H, J 6.0 Hz, CHBr), 7.34 (d, 2H, J 8.1 Hz, CH Ar), 7.91 (d, 2H, J 8.1 Hz,CH Ar), 9.01 (broad s, 1H, NH); 13C NMR (CDCl3) d 20.0 and 20.3 (CH3), 21.7 (CH3Ph), 32.4(CH3CHCH3), 58.1 (CHBr), 128.5 and 129.6 (CH Ar), 134.7 (CS Ar), 145.5 (CCH3 Ar), 166.1(CONH); Anal calcd for C12H16BrNO3S: C 43.12; H 4.83; N 4.19; found C 42.99; H 4.81; N 4.18%.

The synthetic route of Ethyl 2-bromo-3-methylbutanoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ammazzalorso, Alessandra; Tricca, Maria Luisa; Bruno, Isabella; De Filippis, Barbara; Di Matteo, Mauro; Fantacuzzi, Marialuigia; Giampietro, Letizia; Maccallini, Cristina; Mollica, Adriano; Amoroso, Rosa; Synthetic Communications; vol. 45; 22; (2015); p. 2546 – 2554;,
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Related Products of 51329-15-8, These common heterocyclic compound, 51329-15-8, name is Methyl 3,5-dibromobenzoate, 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.

Methyl 3,5-dibromobenzoate (294 mg, 1.0 mmol), 6-methoxy-1,2,3,4-tetrahydroquinoline (179 mg,1.1 mmol), BINAP (31 mg, 0.05 mmol) and palladium acetate (10 mg, 0.05 mmol) were added to 8 ml of toluene, Cs2CO3 (456 mg, 1.4 mmol) was added under nitrogen gas, heated to 100C and reacted for 12 h. A small amount of ethyl acetate was added, insoluble substance was removed by filtration, and the crude product was separated with silica gel column chromatography to obtain Compound 26, which was yellow oil, 255 mg, yield 77%. 1H NMR (CDCl3): delta ppm 1.96 (2H, m, 3′-CH2), 2.76 (2H, t, J = 6.4 Hz, 4′-CH2), 3.61 (2H, t, J = 6.0 Hz, 2′-CH2), 3.78 (3H, s, OCH3), 3.89 (3H, s, OCH3), 6.65 (1H, dd, J = 8.8 Hz and 3.2 Hz, ArH-7′), 6.68 (1 H, d, J = 2.8 Hz, ArH-5′), 6.95 (1 H, d, J = 9.2 Hz, ArH-8′), 7.43 (1 H, t, J = 2.0 Hz, ArH-4), 7.66 (1 H, t, J = 2.0 Hz and 1.6 Hz, ArH-6), 7.66 (1 H, dd, J = 1.2 Hz and 0.8 Hz, ArH-2). MS m/z (%) 376 (M+H+, 100), 378 (M+3+, 91).

Statistics shows that Methyl 3,5-dibromobenzoate is playing an increasingly important role. we look forward to future research findings about 51329-15-8.

Reference:
Patent; Institute Of Pharmacology And Toxicology Academy Of Militaty Medical Sciences P.L.A.; XIE, Lan; WANG, Xiaofeng; LEE, Kuo-Hsiung; EP2857393; (2015); A1;,
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Synthetic Route of 1236357-65-5,Some common heterocyclic compound, 1236357-65-5, name is Methyl 1-(4-bromophenyl)cyclobutanecarboxylate, molecular formula is C12H13BrO2, 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.

To a mixture of 2-aminopyrimidine-5-boronic acid pinacol ester (221 mg, 1.0 mmol), I- 36 (200 mg, 0.74 mmol), Pd-FibreCat-1007 (75 mg, 0.045 mmol) in THF (2.0 mL) at room temperature is added 2M Na2C03 solution (0.75 mL). The mixture is heated in the microwave at 120 C for 30 minutes, allowed to cool to room temperature, and partitioned between EtOAc and H20. The combined organics are washed with brine, filtered, and concentrated in vacuo. The residue is purified by flash chromatography (Si02, 0-100% EtOAc in heptane) to give 1-37 (75 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 1-(4-bromophenyl)cyclobutanecarboxylate, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BERRY, Angela; CHEN, Zhidong; DE LOMBAERT, Stephane; EMMANUEL, Michel Jose; LOKE, Pui Leng; MAN, Chuk Chui; MORWICK, Tina Marie; TAKAHASHI, Hidenori; WO2012/82817; (2012); A1;,
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Synthetic Route of 40876-98-0, The chemical industry reduces the impact on the environment during synthesis 40876-98-0, name is Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of0.01 mol of diethyl oxalylacetate sodium salt, 0.01 molof aromatic aldehyde, and 0.01 mol of urea was heatedat reflux in 10 mL of acetic acid for 2 h. The mixturewas kept for 24 h at room temperature, the precipitatewas filtered off and recrystallized from ethanol.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Gein; Zamaraeva; Volkova; Dmitriev; Russian Journal of Organic Chemistry; vol. 52; 5; (2016); p. 730 – 733; Zh. Org. Khim.; vol. 52; 5; (2016); p. 740 – 743,4;,
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Application of 57381-59-6,Some common heterocyclic compound, 57381-59-6, name is Methyl 5-bromo-2-fluorobenzoate, molecular formula is C8H6BrFO2, 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.

Step 1 (0342) To a solution of 4a (28 g, 113 mmol) in DMF (500 mL) was added naphthalene- 1,6-diol (22 g, 136 mmol) and CS2CO3 (74 g, 226 mmol). The resulting solution was stirred at 100C for 12 h, before it was poured into water and extracted with EA. The combined organic phases were dried over Na2S04. After filtration and concentration, the residue was purified by Si02 chromatography, eluting with petroleum ether: ethyl acetate (100/1-10/1) to give compound 4b (25 g, 59.5%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 5-bromo-2-fluorobenzoate, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KOZLOWSKI, Joseph, A.; YU, Wensheng; HU, Bin; ZHONG, Bin; HAO, Jinglai; WANG, Dahai; LEI, Zhixin; (82 pag.)WO2017/184476; (2017); A1;,
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Related Products of 6091-64-1, 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. 6091-64-1, name is Ethyl 2-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of copper powder (63.5 mg, 1.00 mmol), the aryl halide (500 mumol), 2-aminoethanol (74.9 muL, 1.25 mmol), and TMSN3 (133 muL, 1.00 mmol) in DMA (1 mL) in a 15 mL test tube was stirred under an Ar atmosphere (balloon) at 95 C using a Chemistation personal organic synthesizer (EYELA, Tokyo). After complete consumption of the aryl halide was confirmed by TLC analyses or after 24 h (if the reaction was incomplete within 24 h), the mixture was diluted with EtOAc (10 mL) and then filtered through a Celite pad. The pad was successively washed with EtOAc (20 mL), H2O (25 mL), and concd aq ammonia solution (5 mL). After the two layers were separated, the aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layers were washed with brine (20 mL), dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography with n-hexane/EtOAc or n-pentane/Et2O as the eluent.

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

Reference:
Article; Maejima, Toshihide; Shimoda, Yutaka; Nozaki, Kei; Mori, Shigeki; Sawama, Yoshinari; Monguchi, Yasunari; Sajiki, Hironao; Tetrahedron; vol. 68; 6; (2012); p. 1712 – 1722;,
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Synthetic Route of 104901-43-1, 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. 104901-43-1 name is Methyl 3-bromo-4-methylbenzoate, 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.

Methyl 3-bromo-4-methy. benzoate (50.0 g, 220 mmol) was dissolved in a mixture of 200 ml DMF, 12.5 ml water and 80 ml of tributyl amine. Cesium acetate (20.9 g, 109 mmol) was added and the flask was purged with CO gas. Pd(OAc)2 (2.45 g, 10.9 mmol) and triphenyl phosphine (28.6 g, 109 mmol) were added quickly and the flask was re-purged with CO gas. A balloon filled with CO gas was installed through the septum and the reaction was heated to 95 0C with vigorous stirring overnight. LC-MS showed a 1 :1 ratio of product to starting material. The reaction was diluted with 500 ml of toluene and extracted three times with 300 ml of a NaHCO3 solution. The combined aqueous layer was washed with 100 ml of ethyl acetate, then acidified with 1 N HCI. The resulting precipitate was filtered, washed with 100 ml of water and dried to give a solid (10.8 g, 25% yield). 1H NMR (400 MHz, DMF-O7) delta 13.53 (br s, 1 H), 8.52 (d, J= 1.9 Hz, 1H), 8.03 (dd, J = 9.9, 1.9 Hz, 1H), 7.50 (d, J = 7.9 Hz, 1H), 3.91 (s, 3H), 2.65 (s, 3H); LC/MS, tr = 1.88 minutes (5 to 95% acetonitrile/water over 5 minutes at 1 ml/min, at 254 nm, at 50 0C), ES- MS m/z 195 (M+H). ES-HRMS m/z 193.0473 (M-H calcd for C10H9O4 requires 193.0501).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-bromo-4-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY LLC; WO2006/18735; (2006); A2;,
Ester – Wikipedia,
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Related Products of 106896-49-5, 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. 106896-49-5, name is Methyl 4-amino-3-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: An over-dried vial equipped with stir bar was charged with Pd(OAc)2 (0.0055 g, 0.0245mmol, 0.10 equiv.), dppb (0.020 g, 0.0489 mmol, 0.2 equiv.) and K2CO3 (0.15 g, 0.98 mmol, 4.0equiv.). Freshly distilled toluene was introduced into the vial via syringe and the contents were allowed to stir. A second over-dried vial equipped with a stir bar was charged with cyclopropanol (0.05 g, 0.245 mmol, 1.0 equiv.) and 2-bromoaniline (0.084 g, 0.489 mmol, 2.0equiv.). Freshly distilled toluene was introduced into the vial via syringe and contents allowed to stir. The solution of substrates was added to the solution containing the palladium catalyst. The reaction vial was purged with argon, capped with a rubber septum and heated to 110 C for 24hrs. Upon completion, the reaction mixture was filtered through a pad of celite using EtOAc, and concentrated in vacuo. The crude product was purified by flash column chromatography, eluting with the indicated solvent mixture to afford the desired quinoline product. Purification by flash column chromatography using 20% EtOAc in hexanes provided the desired quinoline as a pale yellow oil (0.051 g, 0.19 mmol) in 76% yield

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 4-amino-3-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Nikolaev, Andrei; Nithiy, Nisha; Orellana, Arturo; Synlett; vol. 25; 16; (2014); p. 2301 – 2305;,
Ester – Wikipedia,
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Reference of 1186-73-8,Some common heterocyclic compound, 1186-73-8, name is Trimethyl methanetricarboxylate, molecular formula is C8H12O6, 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.

Put 300 ml methylbenzene and 60% sodium hydride 3.3g (0.0825 mol) into the 500 ml four-neck flask with reflux condenser pipe, dropping pipette, stirrer and thermometric instrument which is protected by dry nitrogen; and then add 15.8g(0.083 mol) methane tricarboxylic acid triethyl ester into the flask at the temperature of below 80C and protected for 2h by heat preservation; add 33.3g (0.075 mol) bromine sulfonium salts into the flask and then raise the temperature and control the temperature of the entire flask at 80C for a 15h reaction; cool it to the normal temperature and use 5% sulfuric acid to adjust the pH to pH=3; separate the organic layer and extract the water layer by 100 ml methylbenzene for two times; use 40 ml 5% sodium bicarbonate water solution wash the organic layer for two times; dry the oil layer by anhydrous sodium sulfate, filtrate and reduce pressure to recycle faint yellow fluid, finally get the target object-0.2g tri-ssterdibanzyl biotin (95.3% of the theoretical value), and the HPLC measured content is 98.0% with no impurity 5 (hereinafter to be referred as dicarboxylic ester).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Trimethyl methanetricarboxylate, its application will become more common.

Reference:
Patent; Zhejiang Medicine Co., Ltd.; EP2433942; (2012); A1;,
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Reference of 346603-63-2, The chemical industry reduces the impact on the environment during synthesis 346603-63-2, name is Methyl 2-methyl-3-(trifluoromethyl)benzoate, I believe this compound will play a more active role in future production and life.

To a 1 L round bottom flask equipped with a stir bar, nitrogen lines, and pressure equalizing addition funnel, was added lithium aluminum deuteride (LAD) (12 g, 286 mmol). The solid material was taken up in anhydrous tetrahydrofuran (THF) (268 ml) and the resulting suspension placed under a nitrogen atmosphere and the temperature lowered to 0 0C. The addition funnel was then charged with a solution of methyl 2-methyl-3- (trifluoromethyl)benzoate (27 g, 124 mmol) in anhydrous tetrahydrofuran (THF) (107 ml), and the substrate was slowly added, drop-wise, to the LAD suspension over approximately 30 minutes. Upon complete addition, the funnel was removed and the inert atmosphere maintained. The reaction temperature was allowed to warm naturally to ambient over 2 hours with vigorous stirring. The reaction was then quenched with a modified Fieser and Fieser workup (adjusting by multiplying normal lithium aluminum hydride reduction workup amount by .8564) by sequential addition of the following: 10.277 mL water, 10.277 mL of 15 wt % NaOH (aq.) solution, and 30.83 mL water. The resulting mixture was stirred at room temperature for 1 hour to allow the precipitate to form and was then filtered, followed by concentration of the solution, in vacuo, to afford a gel. The gel was suspended in dichloromethane and transferred to a 100 mL round bottom flask. The material was concentrated to a gel and then subjected to high vacuum to afford [2-methyl- 3-(trifluoromethyl)phenyl]methanol-d2 (21.883 g, 114 mmol, 92 % yield) as a white solid 1H NMR (400 MHz, DMSO-J6) delta ppm 2.33 (d, J=I.52 Hz, 3H) 5.26 (s, IH) 7.37 (t, J=7.71 Hz, IH) 7.57 (d, J=7.83 Hz, IH) 7.67 (d, J=7.83 Hz, IH).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 2-methyl-3-(trifluoromethyl)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE LLC; LIN, Hong; LUENGO, Juan, I.; RIVERO, Ralph, A.; SCHULZ, Mark, James; XIE, Ren; ZENG, Jin; WO2010/135504; (2010); A1;,
Ester – Wikipedia,
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