2-BENZYLOXY-5-BROMO-BENZOIC ACID synthesis
- Product Name:2-BENZYLOXY-5-BROMO-BENZOIC ACID
- CAS Number:62176-31-2
- Molecular formula:C14H11BrO3
- Molecular Weight:307.14
850350-09-3
62176-31-2
Benzyl 2-benzyloxy-5-bromobenzoate (18 g, 45.3 mmol) was used as starting material and dissolved in methanol (50 mL). Subsequently, a solution of sodium hydroxide (7.25 g, 181 mmol) in water (20.00 mL) was added to this solution. The reaction mixture was heated to 60°C and the reaction was stirred at this temperature for 2 hours. Upon completion of the reaction, the solvent was removed by rotary evaporation. The residue was diluted with water and washed with ethyl acetate (EA). The aqueous layer was separated and acidified to pH=3 with 4N hydrochloric acid solution and subsequently extracted with ethyl acetate (EA). The organic phases were combined, washed sequentially with water and saturated brine and dried over anhydrous sodium sulfate. Finally, the target product 2-(benzyloxy)-5-bromobenzoic acid (13.46 g, 97% yield) was obtained by concentration under reduced pressure.LCMS analysis showed [M+H]+ m/z 307,309.
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Yield: 97%
Reaction Conditions:
with sodium hydroxide in methanol;water at 60; for 2 h;
Steps:
2-(Benzyloxy)-5-bromobenzoic acid (10b)
To a solution of 10a (18 g, 45.3 mmol) in methanol (50 mL) was added a solution of sodium hydroxide (7.25 g, 181 mmol) in water (20.00 mL). The mixture was heated to 60 °C for 2 hrs. Solvent was removed and the residue was diluted with water, and then washed with EA. The aqueous layer was acidified with 4N HCl solution to pH=3, then extracted with EA. The organic phase was washed with water and brine, dried over Na2SO4 and concentrated in vacuum to give the title compound (13.46 g, 97 % yield). LCMS: 307, 309 [M+H]+.
References:
Ding, Xiao;Stasi, Luigi Piero;Dai, Xuedong;Long, Kai;Peng, Cheng;Zhao, Baowei;Wang, Hailong;Sun, Changhui;Hu, Huan;Wan, Zehong;Jandu, Karamjit S.;Philps, Oliver J.;Chen, Yan;Wang, Lizhen;Liu, Qian;Edge, Colin;Li, Yi;Dong, Kelly;Guan, Xiaoming;Tattersall, F. David;Reith, Alastair D.;Ren, Feng [Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,# 2,p. 212 - 215] Location in patent:supporting information
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62176-31-2
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