B(Br)(Br)Br.[Br:5][C:6]1[C:7]([CH3:16])=[C:8]([C:11]([O:14]C)=[CH:12][CH:13]=1)[CH:9]=[O:10].O.C(OCC)(=O)C.CCCCCC>ClCCl>[Br:5][C:6]1[C:7]([CH3:16])=[C:8]([C:11]([OH:14])=[CH:12][CH:13]=1)[CH:9]=[O:10]
A solution of boron tribromide (12.62 ml, 0.087 mol) in dichloromethane (50 ml) was added to a stirred solution of 3-Bromo-6-methoxy-2-methyl-benzaldehyde (20.0 g, 0.087 mol) in dichloromethane (350 ml) under nitrogen at 0° C. The reaction mixture was stirred for 1.5 hours. Water (400 ml) was added cautiously and the mixture was stirred for 15 min. The organic layer was washed with sodium bicarbonate solution (200 ml), water (200 ml) and brine (200 ml). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give the crude product as orange brown solid. Column chromatography using 3/97 ethyl acetate/hexane yielded 3-Bromo-6-hydroxy-2-methyl-benzaldehyde (13.82 g, 73.6%).
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