Hydrochloric Acid → (5-BroMo-6-chloropyridin-3-yl)Methanol

Participants

Reaction Steps

To a solution of 5-bromo-6-chloronicotinic acid (3.0 g, 13 mmol) in THF (20 mL) at 25° C. was added borane (1.0 M in THF, 25 mL, 25 mmol) dropwise. The solution was stirred for 3 h, after which 1.0 M HCl was added dropwise to quench the reaction and the contents of the flask were transferred to a separatory separation funnel. The organic layer was separated and the aqueous phase further extracted with EtOAc (3×). The combined organic phases were dried over Na2SO4 and concentrated, to furnish 2-chloro-3-bromo-5-hydroxymethylpyridine as a white solid (1.0 g, 37%). GC-MS: Exact mass calcd for C6H6BrClNO [M+H]+, 223. Found 223.

Provenance & Evidence