5,6-Dichloronicotinic acid → (5,6-Dichloropyridin-3-yl)methanol

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Reaction Steps

Borane-tetrahydrofuran complex (1M solution in tetrahydrofuran, 52 ml) was added to a stirred solution of 5,6-dichloronicotinic acid (2 g) in tetrahydrofuran (60 ml) over 20 minutes at 0° C. The reaction mixture was allowed to warm to room temperature over 90 minutes and then cooled to 0° C. and quenched with water (100 ml). The solution was saturated with solid sodium chloride and extracted with ethyl acetate and the combined organic extracts were dried and concentrated in vacuo. The residue was triturated with dichloromethane-50% ethyl acetate and the solid by-product was removed by filtration. The filtrate was concentrated in vacuo and purified by column chromatography using isohexane/ethyl acetate (1:1 v/v) as eluent to yield the product as a white solid (820 mg, 45%). NMR: δ 4.55 (d, 2H), 5.5 (t, 1H), 8.0 (m, 1H), 8.3 (m, 1H); m/z 178.1 (M+H+).

Provenance & Evidence