Category: 89-71-4

Reference of 89-71-4, The chemical industry reduces the impact on the environment during synthesis 89-71-4, name is Methyl 2-methylbenzoate, I believe this compound will play a more active role in future production and life.

(1) To 50 g of Na-X type zeolite dry powder (Zeolum type F-9; 100 meshes or finer, produced by Tosoh Corporation) was added dropwise 7.51 g (50.0 mmol) of methyl 2-methylbenzoate with stirring. Further, 3.9 ml (75 mmol) of bromine was added dropwise thereto at 45~50 C., and the mixture was stirred at 80 C. for 1 hour. To the reaction mixture was added a solution of potassium carbonate (5.5 g) in water (50 ml) and methanol (250 ml). The mixture was stirred at room temperature for 10 minutes and filtered. The residual zeolite powder was washed with warmed hydrous methanol (10%, 250 ml). The filtrate and the washing were combined and concentrated. The residue was diluted with ethyl acetate, washed twice with water, dried and concentrated. The residue (2.98 g) was subjected to silica gel column chromatography (eluted with n-hexane:toluene=10:1 and then 5:1 and then 3:1) to obtain 1.97 g (8.60 mmol) of methyl 5-bromo-2-methylbenzoate as crystals.

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-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sumitomo Chemical Company, Limited; US6489487; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 89-71-4,Some common heterocyclic compound, 89-71-4, name is Methyl 2-methylbenzoate, molecular formula is C9H10O2, 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.

2-Methyl-benzoic acid methyl ester (1.50 g 10 mmol), N-bromo-succinimide (1.96 g, 11 mmol) and 2,2′-azobis(2-methyl-propionitrile) (AIBN) (25 mg, 0.15 mmol) were dissolved in chloroform (3 ml). The solution was heated at reflux for 16 hours cooled and the solvent evaporated in vacuo. The residue was purified by silica gel chromatography using a gradient of ethyl acetate/hexane (1-2 %) as eluent. Pure fractions were collected and the solvent evaporated in vacuo affording 2.05 g (89 %) of 2-bromomethyl-benzoic acid methyl ester as a solid. 1H-NMR (CDCl3): delta 7.97 (d, 1H, J = 7.6 Hz), 7.45-7.52 (m, 2H), 7.38 (dt, 1H, J = 1.2 Hz and J = 7.6 Hz), 4.96 (s, 2H), 3.95 (s, 1H). To a solution of 2-amino-5-(S)-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester (100 mg, 0.20 mmol) and pyridine (0.18 ml, 2.0 mmol) in acetonitrile (1 ml) at room temperature was added benzyl chloroformate (0.28 ml, 2.0 mmol) in 10 aliquots over 48 hours. The solution was then taken into ethyl acetate (30 ml), washed with 0.5 N hydrochloric acid (3×10 ml), saturated sodium bicarbonate (3 x 10 ml), brine (10 ml), dried (MgSO4) and filtered. The solvent was evaporated in vacuo. The resulting oil crystallized upon standing for 2 days. The precipitate was filtered off and washed with diethyl ether (3 x 1 ml) affording after drying in vacuo 59 mg (47 %) of 2-benzyloxy-carbonylamino-5-(S)-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester as a solid. 1H-NMR (CDCl3): delta 10.60 (s, 1H), 7.60-7.92 (m, 4H), 7.38 (m, 5H), 5.26 (s, 2H), 4.30-5.10 (m, 3H), 3.40-4.00 (m, 2H), 1.57 (m, 9H), 1.15 (m, 9H). To a solution of 1 N hydrochloric acid in ethyl acetate (1.0 ml) was added 2-benzyloxy-carbonylamino-5-(S)-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester (52 mg, 0.08 mmol). The solution was stirred at room temperature for 48 hours. A precipitate was filtered off which afforded 42 mg (90 %) of 2-benzyloxy-carbonylamino-5-(S)-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester hydrochloride as a solid. 1H-NMR (DMSO-d6): delta 10.45 (s, 1H), 9.40 (s, 1H), 9.25 (s, 1H), 7.89 (m, 4H), 7.39 (m, 5H), 5.22 (s, 2H), 4.39 (d, 1H, J = 15 Hz), 4.28 (m, 1H), 3.95 (m, 2H), 3.79 (m, 1H), 3.20 (m, 1H), 2.70 (m, 1H), 1.48 (s, 9H). To a solution of the above 2-benzyloxy-carbonylamino-5-(S)-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester hydrochloride (42 mg, 0.072 mmol) in ethanol (0.5 ml) was added hydrazine (68 mul, 0.22 mmol). The solution was stirred at 80 C for 5 hours and at room temperature for 16 hours. The mixture was filtered and the filtrate evaporated in vacuo. The residue was extracted with dichloromethane (5 x 1 ml). The combined dichloromethane washes were evaporated in vacuo affording 20 mg (67 %) of 5-(S)-aminomethyl-2-benzyloxy-carbonylamino-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester as an oil. 1H-NMR (CDCl3): delta 10.55 (bs, 1H), 7.37 (m, 5H), 5.23 (s, 2H), 3.92 (s, 2H), 2.60-3.10 (m, 3H), 1.53 (s, 9H). To a solution of the above 5-(S)-aminomethyl-2-benzyloxy-carbonylamino-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester (20 mg, 0.048 mmol) in acetonitrile (1 ml) at 0 C was added diisopropylethylamine (18 l, 0.15 mmol) and 2-bromomethyl-benzoic acid methyl (12 mg, 0.048 mmol). The solution was stirred at 0 C for 3 hours and at room temperature for 16 hours. Di-tert-butyl dicarbonate (21 mg, 0.096 mmol) was then added to the solution. The solution was then stirred at room temperature for 16 hours. The solution was taken into ethyl acetate (30 ml), washed with 0.5 N hydrochloric acid (3 x 10 ml), saturated sodium bicarbonate (3 x 10 ml) and brine (10 ml), dried (MgSO4) and filtered. The solvent was evaporated in vacuo. The solid residue was purified by silica gel chromatography using a 5 % mixture of ethyl acetate/hexane as eluent. Pure fractions were collected and the solvent evaporated in vacuo affording 10 mg (33 %) of 2-(benzyloxycarbonylamino)-5-(S)-(1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester as a solid. 1H-NMR (CDCl3): delta 10.59 (s, 1H), 7.81 (m, 1H), 7.52 (m, 1H), 7.39 (m, 7H), 5.25 (s, 1H), 4.22-5.00 (m, 4H), 4.40-4.80 (m, 2H), 2.80-3.10 (m, 2H), 1.55 (s, 9H), 1.25 (s, 9H). To a solution of the above 2-benzytoxycarbonylamino-5-(S)-(1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester (9 mg, 0.014 mmol) in methanol (2 ml) was added 10 % Pd/C (4 mg). The mixture was stirred under hydrogen (1 atm.) for 3 hours and then filtered. The filtrate was evaporated in vacuo affordi…

The synthetic route of 89-71-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVO NORDISK A/S; Ontogen Corporation; EP1214324; (2006); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 89-71-4, name is Methyl 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. COA of Formula: C9H10O2

To a mixture of methyl 2-methylbenzoate (5.0 g, 0.033 mmol) and N- bromosuccinimide (5.9 g, 0.033 mmol) in CCU (50 ml_) was added benzoyl peroxide (0.04 g, 0.00016 mmol). The mixture was heated to reflux for 1.5 h, cooled to room temperature, filtered through Celite, and concentrated to afford methyl 2- (bromomethyl)benzoate (7.2 g, ca. 94% mass recovery), which was contaminated with ca. 14% unreacted starting material and was used without purification.

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

Reference:
Patent; WYETH; WO2006/128142; (2006); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 89-71-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 89-71-4 as follows.

A mixture of methyl o-toluate (13.5 g, 89.9 mmol), NBS (17.6 g, 98.9 mmol), and benzoyl peroxide (50 mg, 0.2 mmol) in carbon tetrachloride (250 mL) was heated at reflux over the weekend. The reaction mixture was allowed to cool, and it was then filtered. The solvents were evaporated under reduced pressure and the residue was purified by chromatography, eluting with 3% ethyl acetate/hexanes to give 2-bromomethyl-benzoic acid methyl ester (7.7 g, 37%) as a white solid. 1HNMR (CDCl3): delta 7.97 (dd, J=1.5 Hz, 8.0 Hz, 1H), 7.49 (m, 2H), 7.38 (dt, J=1.5 Hz, 8.0 Hz, 1H), 4.96 (s, 2H), 3.94 (s, 3H). MS (APCI+): 231 (100), 229 (93).

According to the analysis of related databases, 89-71-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chu, Chang An; Gillespie, Paul; Tilley, Jefferson Wright; US2004/266856; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 89-71-4, name is Methyl 2-methylbenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: 89-71-4

General procedure: To a solution of 6.0 g (0.04 mol) of methyl 2-methylbenzoate derivatives in 38 mL of chloroform, 7.5 g (0.042 mol) of N-bromosuccinimide and 0.078 g of benzoyl peroxide were added and carefully warmed up to 65 C until reaction started. Then the mixture was refluxed for 5 h. After cooling down to room temperature, the deposit of succinimide was filtered. The solvent was removed under reduced pressure and the crude product was used in the next step without further purification. To a solution of functionalized methyl 2-(bromomethyl)benzoate (6.55 mmol), substituted phenol (8.5 mmol), K3PO4 (16.4 mmol) and toluene 20 mL were added to Schlenk under argon. The resulting solution was stirred to 110 C for 5 h. The progress of the reaction was monitored by TLC. The mixture was extracted with EtOAc, washed with water, brine and the combined organic layers were dried over anhydrous Na2SO4and the solvent was removed under reduced pressure. The crude product was used in the next step without further purification. To the solution of the ester (0.015 mol) in MeOH (73 mL), was added 13 mL aqueous KOH (20%) and refluxed at 80C for 5 h. MeOH was removed and the aqueous phase was washed with DCM. After acidifying with HCl (10%) the deposit was collected and washed with water.

The synthetic route of 89-71-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Scoccia, Jimena; Castro, M. Julia; Faraoni, M. Belen; Bouzat, Cecilia; Martin, Victor S.; Gerbino, Dario C.; Tetrahedron; vol. 73; 20; (2017); p. 2913 – 2922;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 89-71-4, A common heterocyclic compound, 89-71-4, name is Methyl 2-methylbenzoate, molecular formula is C9H10O2, 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.

Placed in a 20L reaction vessel was petroleum ether, o-methyl benzoate, N- bromosuccinimide. Use a water bath to control temperature at 15 deg.C. Under stirring, react for 2.5h. Using known separation methods, separated o halomethyl benzoate.

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; Suzhou Huanghe Pharmaceutical Co., Ltd.; Su, Zixuan; Qu, Xiaoming; Xiao, Zuhua; (16 pag.)CN105330639; (2016); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 89-71-4, name is Methyl 2-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H10O2

To a solution of methyl 2-methylbenzoate (5g, 0. 033mol) in carbon tetrachloride (85ml) was added n-bromosuccinimide (5.93g, 0. 033mol) and benzoyl peroxide (0.22g, 0. 9mol). The reaction was refluxed for 4 hr. The reaction was cooled to room temperature. The white precipitate was filtered and the solvent removed. The oil was dissolved in ET2O and cooled to-78C The product precipitated and collected yielding v (5. 86G, 77%).

According to the analysis of related databases, 89-71-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHROMA THERAPEUTICS LIMITED; WO2004/101506; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics