Tag: M.W=200-300

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. 23062-51-3, name is Methyl 4-bromobicyclo[2.2.2]octane-1-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 4-bromobicyclo[2.2.2]octane-1-carboxylate

To the title compound from the Preparative Example 55, Step A (677 mg) was added 10% aqueous NaOH (65 niL). The mixture was stirred at 100C (temperature of the oil bath) for 42 h, concentrated to 15 mL and diluted with IN aqueous HCl (3O mL). The resulting mixture was acidified to pH 1 with 12N aqueous HCl and extracted with EtOAc (5 x 70 mL). The combined organic phases were dried (MgSO4), filtered and concentrated to afford the title compound (540 mg, 89%). [MH]+ = 171

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; ALANTOS-PHARMACEUTICALS, INC.; WO2006/128184; (2006); A2;,
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41841-16-1, name is Methyl 2-(4-bromophenyl)acetate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 41841-16-1

A solution of methyl 2-(4-bromophenyl)acetate (6g, 30mmol) in tetrahydrofuran (67.2ml, 0.39/W) was added 1 M potassium t-butoxide in tetrahydrofuran (57.6ml, 57.6mmol). Reaction mixture was cooled to 00C and methyl iodide (3.59ml, 57.6mmol) was added drop wise. After addition was complete, reaction was slowly warmed up to room temperature and stirred for 16 hours. Reaction mixture was then carefully quenched with 1 M hydrochloric acid and concentrated. Reaction was diluted with water and extracted with ethyl acetate. Pooled organics were washed with water and brine and then dried over sodium sulfate, filtered and concentrated to give a crude dark oil. Crude product purified on silica gel eluting with 0%-5% ethyl acetate in heptane to give methyl 2-(4-bromophenyl)-2-methylpropanoate (1 D-1 ) (6.44g, 92%) as a yellow oil 1 H NMR (400 MHz, CHLOROFORM-d) d ppm 1.54 (s, 6 H) 3.63 (s, 3 H) 7.19 (d, J=8.78 Hz, 2 H) 7.43 (d, J=8.98 Hz, 2 H)MS(LC-MS) 371.2 (M+1 )

The synthetic route of 41841-16-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; ASPNES, Gary, Erik; DOW, Robert, Lee; MUNCHHOF, Michael, John; WO2010/86820; (2010); A1;,
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Application of 135613-33-1, 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. 135613-33-1, name is Ethyl 3-(2-bromophenyl)propanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(b) 2-(2-thiazolinylthio)-hydrocinnamic acid ethyl ester: 1.4 ml of triethylamine are added dropwise to a solution of 1.8 g of 2-mercapto-1,3-thiazoline and 2.6 g of 2-bromo-hydrocinnamic acid ethyl ester in 15 ml of THF and the whole is stirred under reflux for 6 hours. The reaction mixture is filtered, the filtrate is concentrated by evaporation and the residue is partitioned between ethyl acetate and water. The organic phase is washed with water, dried, concentrated by evaporation and purified by chromatography on silica gel with eluant R. Rf (W)=0.67.

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, Ethyl 3-(2-bromophenyl)propanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ciba-Geigy Corporation; US4758584; (1988); A;,
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These common heterocyclic compound, 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate, 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. SDS of cas: 35450-36-3

A mixture of methyl 2-bromo-5-methoxybenzoate (3.0 g, 12.2 mmol), vinylboronic acid (2.26 g, 14.7 mmol), K2CC>3 (5.08 g, 36.72 mmol) and Pd(dppf)Cl2-DCM (500 mg, 0.61 mmol) in 1,4-dioxane/H2Patent; CTXT PTY LIMITED; STUPPLE, Paul, Anthony; LAGIAKOS, Helen, Rachel; FOITZIK, Richard, Charles; CAMERINO, Michelle, Ang; NIKOLAKOPOULOS, George; BOZIKIS, Ylva, Elisabet, Bergman; KERSTEN, Wilhelmus, Johannes, Antonius; WALKER, Scott, Raymond; HUBERT, Jonathan, Grant; (0 pag.)WO2020/2587; (2020); A1;,
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Related Products of 110661-91-1,Some common heterocyclic compound, 110661-91-1, name is tert-Butyl 4-bromobutanoate, molecular formula is C8H15BrO2, 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.

Part A Preparation of 6-[(5-Hydroxypentyl)oxy]-2-(4-t-butoxy-4-oxobutyloxy)benzenepropanoic Acid Methyl Ester A mixture of 2-hydroxy-6-[(5-hydroxypentyl)oxy]-benzenepropanoic acid methyl ester (2.04 g, 7.23 mmol) (as described by Cohen, N. EP Appl. 531,823), t-butyl 4-bromobutyrate (1.93 g, 8.67 mmol), and K2CO3 (2.29 g, 16.6 mmol) in DMSO (60 mL) was stirred at ambient temperatures under nitrogen for 21 h. The solids were removed by filtration and the filtrate was diluted with water (100 mL), and extracted with EtOAc (3*100 mL). The combined organic extracts were washed with water and sat. NaCl, dried (MgSO4), and concentrated to give product as a yellow oil (2.98 g). A portion (487 mg) was purified by silica gel flash chromatography (40:60 EtOAc/hexanes) to give the title compound as a colorless oil (367 mg, 73.3%). 1H NMR (CDCl3): 7.08 (t, J=8.2 Hz, 1H), 6.48 (d, J=8.2 Hz, 2H), 4.00-3.89 (m, 4H), 3.70-3.62 (m, 5H), 3.04-2.93 (m, 2H), 2.50-2.39 (m, 4H), 2.11-1.99 (m, 2H), 1.88-1.75 (m, 2H), 1.72-1.52 (m, 5H), 1.43 (s, 9H); MS: m/e 447.3 [M+Na].

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

Reference:
Patent; Bristol-Myers Squibb Pharma Company; US6416733; (2002); B1;; ; Patent; Carpenter JR., Alan P.; US2003/3049; (2003); A1;; ; Patent; Barrett, John Andrew; Cheesman, Edward Hollister; Harris, Thomas David; Liu, Shuang; Rajopadhye, Milind; Sworin, Michael; US2003/124053; (2003); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1000342-11-9, category: esters-buliding-blocks

01629] Step 4: Synthesis of methyl 5-bromo-2-methyl-3-[(oxan-4-yl)amino]benzoate[01630] To a solution of methyl 3-amino-5-bromo-2-methylbenzoate (3.0 g, 12 mmol) in 1 ,2- dichloroethane (48 ml) under nitrogen, was added oxan-4-one (2.3 ml, 25 mmol) followed by acetic acid (4.2 ml, 74 mmol). The reaction mixture was stirred for 5 minutes before the addition of sodium triacetoxyborohydride (7.8 g, 37 mmol). After stirring for 64 hours, deionized water (100 ml) was added and the mixture was neutralized with solid NaHC03. The phases were separated and the aqueous layer was extracted with EtOAc (4 x 50 ml). The combined organic extracts were dried over MgS04, filtered and concentrated in-vacuo. The residue was purified by flash column chromatography (50g silica, Isolute cartridge, 10-30% EtOAc:Heptanes) to give the title compound (3.5 g 85%) as a white solid. LC-MS 99.8m/z= 327.9, 328.9, 329.9, 330.9; NMR (500 MHz, Chloroform-d) delta ppm 7.24 (d, J=1.73 Hz, 1 H) 6.85 (d, J=l .58 Hz, 1 H) 4.03 (dt, J=l 1 .82, 3.3 1 Hz, 2 H) 3.88 (s, 3 H) 3.66 (br.s., 1 H) 3.56 (td, J=U .55, 1 .97 Hz, 2 H) 3.47 – 3.55 (m, 1 H) 2.24 (s, 3 H) 2.06 (d, J= 13.56 Hz, 2 H) 1.47 – 1 .60 (m, 2 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-5-bromo-2-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); A1;,
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These common heterocyclic compound, 99548-55-7, name is Methyl 4-bromo-2-methylbenzoate, 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. SDS of cas: 99548-55-7

Example 17: 4-cyano-2-methylbenzoic acid methyl ester; To a solution of 4-bromo-2-methylbenzoic acid (108 g, 471 mmol) inLambda/,Lambda/-dimethylformamide (4 L) under a nitrogen atmosphere was added zinc (II) cyanide (88.5 g, 753.6 mmol) and tetrakis(triphenylphosphine)palladium (65 g, 56.60 mmol). The reaction mixture was stirred at 1000C for 16 hours. The reaction mixture was diluted with toluene and the phases were separated. The aqueous phase was extracted twice with toluene. The combined organic phases were washed with brine and saturated aqueous ammonium hydroxide, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate / cyclohexane 1 :5) to give 4-cyano-2- methylbenzoic acid methyl ester (73 g, 89percent yield). 1H NMR (400 MHz, CDCl3): 7.78 (d, IH), 7.52 (m, 2H), 3.92 (s, 3H), 2.62 (s, 3H) ppm.

The synthetic route of Methyl 4-bromo-2-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; MAIENFISCH, Peter; GODFREY, Christopher Richard Ayles; JUNG, Pierre Joseph Marcel; HUETER, Ottmar Franz; RENOLD, Peter; WO2010/127928; (2010); A1;,
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Electric Literature of 6091-64-1, 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. 6091-64-1, name is Ethyl 2-bromobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Example 4 To a solution (25 ml) of 2-(4-trifluoromethylphenyl)furan (3.18 g) in tetrahydrofuran was added dropwise n-butyl lithium (1.6 M solution in hexane, 10.0 ml) under an argon atmosphere at -78C. This mixed solution was heated to room temperature, and a solution (30 ml) of zinc chloride (2.25 g) in tetrahydrofuran was added. This mixture was stirred for 1 hr., and then ethyl 2-bromobenzoate (2.38 ml) and tetrakis (triphenylphosphine)palladium (0.433 g) were added. This mixture was stirred overnight under an argon atmosphere, and then poured into 0.5 M hydrochloric acid. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1, volume ratio) to give ethyl 2-[5-(4-trifluoromethylphenyl)-2-furyl]benzoate (2.54 g, yield 47%) as a pale-yellow oil. NMR (CDCl3) delta: 1.12 (3H, t, J = 7.2 Hz), 4.27 (2H, q, J = 7.2 Hz), 6.70 (1H, d, J = 3.6 Hz), 6.87 (1H, d, J = 3.6 Hz), 7.41 (1H, dt, J = 1.4, 7.4 Hz), 7.53 (1H, dt, J = 1.4, 7.4 Hz), 7.61-7.79 (6H, m).

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-bromobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1405636; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 609-12-1, A common heterocyclic compound, 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, molecular formula is C7H13BrO2, 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.

General procedure: General Method 4C: N-Alkylation of 2-pyridinonederivatives with the appropriate 2-bromo-or 2-chloropropanoic ester derivativesin the presence of sodium hydride/lithium bromide Under argon and at 0 C, 1.25eq. of sodium hydride (60% in mineral oil) were added to a solution of 1.0 eq.of the appropriate 2-pyridinone derivative in dimethylformamide (5-10 ml/mmol),and the mixture was stirred at 0 C for 10-20 min. 2.0 eq. of lithium bromidewere then added, the reaction mixture was stirred at RT for 15 min, 1.25 eq. ofthe appropriate 2-bromo- or 2-chloropropanoic ester derivative were added andthe mixture was stirred at 65 C. After removal of the DMF and addition ofwater/ethyl acetate and phase separation, the organic phase was washed withwater, dried (sodium sulphate), filtered and concentrated under reducedpressure. The crude product was then purified either by flash chromatography(silica gel 60, mobile phase: cyclohexane/ethyl acetate mixtures or dichloromethane/methanol mixtures) or bypreparative HPLC (Reprosil C18, water/acetonitrile gradient or water/methanolgradient).500 mg (2.9 mmol) of 4-bromopyridin-2(1H)-one and 841mg (4.02 mmol) of ethyl 2-bromo-3-methylbutanoate (racemate) in the presence of1.15 eq. of sodium hydride and 2.3 eq. of lithium bromide were reactedaccording to General Method 4C. Yield: 260 mg (purity92%, 28% of theory)

The synthetic route of 609-12-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; Rurik, Jujane; Hilliswe, Alexander; Strassburke, Yulia; Hidemeyer, Stefan; Smith, Martina Victoria; Schlemmer, Karl-Heinz; Terstigen, Adrian; Buchmuller, Anya; Gerdes, Hirstoph; Schappe, Martina; Kinchel, Tom; Teller, Henryk; Shirok, Hartmut; Klar, Juergen; Jimenez, Nunez Eloisa; (352 pag.)KR2015/137095; (2015); A;,
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Adding a certain compound to certain chemical reactions, such as: 35065-86-2, name is 3-Bromophenyl acetate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 35065-86-2, Recommanded Product: 3-Bromophenyl acetate

Acetylated intermediate and aluminum trichloride (2.3g) with vigorous stirringThe mixture was heated to 160 C under an argon atmosphere for 2 h in a 50 mL single-mouth bottle, cooled to room temperature, and extracted with a 3 M hydrochloric acid solution and ethyl acetate.After the organic phase is washed with water and a saturated sodium chloride solution,Dry over anhydrous sodium sulfate.After concentration, column chromatography gave 1 g of pale yellow solid.

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, 3-Bromophenyl acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Changsen Pharmaceutical Co., Ltd.; Wang Zhe; Fan Guoqin; Zeng Zhihong; Wang Xiaoguang; Jiang Rongzhen; (64 pag.)CN109678796; (2019); A;,
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Ester – an overview | ScienceDirect Topics