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

Temperature

0 °C

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.

1. waitat room temperature for 2 h
2. stirringthe mixture stirred at room temperature overnight
3. customThe organic layer was separated
4. extractionthe aqueous layer extracted with dichloromethane
5. washThe combined organic layer was washed with water
6. dry with materialdried over anhydrous MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customdried

ORD record

ord-712e75393f424e6db618aaa3d59e0b6f

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08178565B2