Hydrochloric Acid → (5,6-Dichloropyridin-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

Borane tetrahydrofuran complex (15.4 mL, 15.4 mmol) was added to a stirred solution of 5,6-dichloronicotinic acid (2.46 g, 12.8 mmol) in anhydrous THF (15 mL) at 0° C. The mixture was stirred at 0° C. for 30 min while the mixture became orange in color and then at RT for 3 h. An additional portion of borane tetrahydrofuran complex (15.4 mL, 15.4 mmol) was added and the mixture was stirred at RT for 16 h. The mixture was then carefully poured into a cold 1 N aqueous HCl solution and extracted with DCM. The organic layer was dried (Na2SO4), filtered and the solvents evaporated to yield 5,6-dichloro-pyridin-3-yl)-methanol (1.64 g, 68%) as a pale yellow wax which was used in next reaction without further purification.

Provenance & Evidence