[BH4-].[Li+].C[O:4][C:5](=O)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[C:7]=1[O:13][CH3:14].CO>CCOCC>[Br:12][C:8]1[C:7]([O:13][CH3:14])=[C:6]([CH2:5][OH:4])[CH:11]=[CH:10][CH:9]=12.4 g of lithium borohydride (LiBH4) was added to a solution of 5.3 g of 3-bromo-2-methoxy-benzoic acid methyl ester 5 in 200 mL of ether (Et2O) at 0° C. After stirring for 5 minutes, 5 mL of methanol was added. The reaction mixture was warmed to room temperature and kept there for 2.5 hours. Thereafter, 2.4 g more of lithium borohydride was added. The reaction mixture was quenched with aluminum chloride. After standard aqueous work up, and silica gel column purification (hexane/ethyl acetate 2:1), 4.0 g of 3-bromo-2-methoxy-phenyl-methanol 6 was obtained.
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