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(5-bromopyridin-3-yl)methanol (475 mg, 2.5 mmol) and triphenylphosphine (1.3 g, 5 mmol) were combined in methylene chloride (20 mL) and cooled to 0° C. carbon tetrabromide (927 mg, 2.8 mmol) was introduced in portions and the reaction was maintained at 0° C. for 1 h. The reaction was concentrated and purified by column chromatography on silica gel (0 to 50% ethyl acetate/hexanes) to produce 254 mg (41%) as a white solid. 1H-NMR (D6DMSO, 400 MHz) δ 8.65 (s, br, 2H), 8.18 (s, 1H), 4.73 (s, 2H). Mass spec.: 249.89 (MH)+.

1. additionwas introduced in portions
2. concentrationThe reaction was concentrated
3. custompurified by column chromatography on silica gel (0 to 50% ethyl acetate/hexanes)
4. customto produce 254 mg (41%) as a white solid