Synthesis
General procedure for the synthesis of 2-amino-5-bromobenzenemethanol from 2-amino-5-bromobenzoic acid: 2-amino-5-bromobenzoic acid (10 g, 46.3 mmol) was added to a 500 mL reaction vial, dissolved in anhydrous tetrahydrofuran (THF) (100 mL), and the reaction was carried out under nitrogen protection. Borane tetrahydrofuran solution (1 M, 231 mL, 231 mmol) was added slowly and dropwise under ice bath cooling conditions. After the dropwise addition, the reaction mixture was gradually warmed to room temperature and stirred overnight. Upon completion of the reaction, water (150 mL) was added slowly under cooling in an ice bath to quench the reaction. The resulting mixture was extracted with ethyl acetate, the organic layer was washed sequentially with water and sodium hydride solution, and then dried with anhydrous sodium sulfate. Finally, the solvent was removed by evaporation under reduced pressure to afford the target product 2-amino-5-bromobenzenemethanol (9.7 g, 100% yield) as a white solid.
References
[1] ACS Catalysis, 2013, vol. 3, # 4, p. 622 - 624
[2] Chemical Communications, 2017, vol. 53, # 1, p. 216 - 219
[3] Organic Letters, 2017, vol. 19, # 12, p. 3219 - 3222
[4] Patent: CN107304201, 2017, A. Location in patent: Paragraph 0061; 0064
[5] Tetrahedron Letters, 2017, vol. 58, # 40, p. 3795 - 3799
