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

Temperature

0 °C

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.

1. waitat RT for 3 h
2. additionAn additional portion of borane tetrahydrofuran complex (15.4 mL, 15.4 mmol) was added
3. stirringthe mixture was stirred at RT for 16 h
4. extractionextracted with DCM
5. dry with materialThe organic layer was dried (Na2SO4)
6. filtrationfiltered
7. customthe solvents evaporated
8. customto yield 5,6-dichloro-pyridin-3-yl)-methanol (1.64 g, 68%) as a pale yellow wax which
9. customwas used in next reaction without further purification

ORD record

ord-b30889b2b16842bd8da9522e52e0a0f8

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08853237B2