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

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5,6-dichloronicotinic acid (9.6 g, 50 mmol) in anhydrous tetrahydrofuran (THF; 50 mL) cooled in an ice-water bath was rapidly added 1 M BH3 solution in THF (60 mL, 60 mmol) via a syringe. The mixture was stirred at 0° C. for 30 min while the mixture became orange in color and then at room temperature for 2 h. An additional portion of 1 M BH3 solution in THF (50 mL, 50 mmol) was added and the mixture stirred at room temperature overnight. The mixture was then carefully poured into cold aqueous 1 N HCl solution (100 mL). The organic layer was separated and the aqueous layer extracted with dichloromethane. The combined organic layer was washed with water, dried over anhydrous MgSO4, filtered, concentrated, and dried to give the desired 2,3-dichloro-5-hydroxymethylpyridine as a yellow oil. GC-MS: mass calcd for C6H5Cl2N [M]+162. Found 162.

Provenance & Evidence