Reference of 52727-57-8,Some common heterocyclic compound, 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, molecular formula is C8H8BrNO2, 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- (morpholin-4-ylsulfonyl) benzoic acid (271 mg, 1.0 mmol) was suspended in [CH2C12] (10 mL) and (COCl) 2 added (725 mg, 5.7 mmol). A catalytic amount [OF DMF] was then added and the mixture stirred for 4 hrs. The solvent was then removed in vacuo to give the acid chloride as an oil. The oil was dissolved in [CHC13] (10 mL). Methyl 2- amino-5-bromobenzoate (230 mg, 1.0 mmol) was added followed by pyridine [(1] mL). The solution was stirred at room temperature for an additional 12 hrs then poured into 1 M HC1 (20 [ML)] and extracted with EtOAc (3 x 20 mL). The combined organic solutions were dried over Na2S04 and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (20% EtOAc in hexane) to provide 367 mg of the desired methyl ester (76%). The ester was treated with [LIOH] in 1: 1: 1 THF/MeOH/H20 for 12 hrs followed by acidification and extraction with EtOAc. The organic solution was dried over NazS04 and then concentrated in vacuo. The title compound (328 mg, 92%, 70% overall) was obtained as a white solid after recrystalization from [MEOH.] H NMR (400 MHz, DMSO) 2.93 (m, [4H),] 3.65 [(M,] 4H), 7.88 (dd, 1H), 7.90 (d, 1H), 8.00 (d, [1H),] 8.13 (d, 1H), 8.25-8. 29 [(M,] [2H),] 8. 59 (d, 1H), 12.21 (s, 1H).
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-amino-5-bromobenzoate, its application will become more common.
Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18414; (2004); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics