[CH3:1][O:2][C:3]1[C:8]([CH2:9]O)=[CH:7][CH:6]=[C:5]([CH3:11])[N:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:32]>ClCCl>[Br:32][CH2:9][C:8]1[C:3]([O:2][CH3:1])=[N:4][C:5]([CH3:11])=[CH:6][CH:7]=1To a solution of (2-methoxy-6-methylpyridin-3-yl)methanol (4.7 g, 30.7 mmol) in dichloromethane (150 mL) was added triphenylphosphine (12.1 g, 46.0 mmol). The mixture was cooled in an ice bath with stirring under an atmosphere of nitrogen. Carbon tetrabromide (15.3 g; 46.0 mmol) was added and the mixture was stirred for 90 minutes. The mixture was concentrated under reduced pressure and purified using column chromatography on silica, eluting with dichloromethane/hexanes (1:1) to give 3-(bromomethyl)-2-methoxy-6-methylpyridine (2.0 g).
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