2316-64-5

white to light brown crystalline powder or flakes

The general procedure for the synthesis of 5-bromo-2-hydroxybenzenemethanol from 5-bromosalicylaldehyde was as follows: according to the improved synthetic method reported in the literature, 5-bromo-2-hydroxybenzenecarboxaldehyde (10.1 g, 50 mmol) was first dissolved in 250 mL of ethanol at 0 °C. Subsequently, NaBH4 (1.88 g, 50 mmol) was added to the stirring solution in batches (0.3 g each). The reaction mixture was stirred continuously for 18 hours at room temperature. Upon completion of the reaction, ethanol was evaporated under reduced pressure conditions (102 mbar) and the light yellow solid obtained was dissolved in 200 mL of saturated aqueous NH4Cl solution. The crude product was extracted by ether (three times, 80 mL each). The combined organic phases were washed with brine (three times, 20 mL each) and dried with MgSO4 for 2 hours. After drying, the MgSO4 was removed by filtration and the excess solvent was evaporated under reduced pressure (102 mbar). The product was purified by fast chromatography on a silica gel column with hexane/ethyl acetate (8:2, v/v) as eluent. Eventually, evaporation of the solvent gave a colorless solid product (8.52 g, 84% yield).

[1] Tetrahedron Asymmetry, 2011, vol. 22, # 13, p. 1395 - 1399
[2] Journal of Chemical Research - Part S, 2003, # 6, p. 335 - 339
[3] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2003, vol. 58, # 12, p. 1220 - 1226
[4] Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 2, p. 307 - 315
[5] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2005, vol. 60, # 4, p. 453 - 457