Category: 104901-43-1

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,
Ester – an overview | ScienceDirect Topics

104901-43-1,Some common heterocyclic compound, 104901-43-1, name is Methyl 3-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.

A pressure vessel was charged with methyl 3-bromo-4-methylbenzoate (5.0 g, 22 mmol), DMF (20 ml), water (1.25 ml) and tributylamine (8 ml, 34 mmol). Cesium acetate (2.1 g, 11 mmol) was then added and the flask was purged with N2. Palladium acetate (0.25 g, 1.0 mmol) and triphenylphosphine (2.9 g, 11 mmol) were added and the flask was purged with CO gas. The reaction mixture was then heated at 90 C. under 20 psi of CO gas with vigorous stirring overnight. The reaction mixture was diluted with 50 mL of toluene and extracted with saturated NaHCO3 (3*50 ml). The combined aqueous layer was washed with EtOAc (10 mL), then acidified using 2 N HCl to pH 5. The volume was reduced to about 50 mL and the resulting precipitate was collected by filtration, washed with water and dried to give 5-(methoxycarbonyl)-2-methylbenzoic acid as a white solid. MS (ESI, pos. ion) m/z: 193.1 (M-1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 104901-43-1, its application will become more common.

Reference:
Patent; Dimauro, Erin F.; Bemis, Jean E.; Chaffee, Stuart C.; Chen, Ning; Hu, Essu; Kunz, Roxanne; Martin, Matthew W.; McGowan, David C.; Rumfelt, Shannon; US2007/72862; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics