Sodium borohydride → (2-Chloro-4,6-difluorophenyl)methanol

Sodium borohydride (1.42 g, 37.5 mmol) was added in portions to an ice-cooled solution of 2-chloro-4,6-difluorobenzaldehyde (6.70 g, 38.0 mmol) in methanol (56 ml); once addition was complete the reaction was warmed to rt over 1 h and then concentrated in vacuo. The residue was partitioned between ether and saturated sodium bicarbonate solution, the phases were separated and the aqueous phase extracted with more ether. The combined organic phases were washed with H2O, dried with MgSO4 and concentrated in vacuo to yield the crude product as an oil which was diluted with pentane (20 mL) and allowed to stand in a freezer overnight. The liquors were decanted from the resultant white crystals which were then dried in vacuo to yield the title compound (5.60 g, 31.4 mmol).

1. additiononce addition
2. concentrationconcentrated in vacuo
3. customThe residue was partitioned between ether and saturated sodium bicarbonate solution
4. customthe phases were separated
5. extractionthe aqueous phase extracted with more ether
6. washThe combined organic phases were washed with H2O
7. dry with materialdried with MgSO4
8. concentrationconcentrated in vacuo
9. customto yield the crude product as an oil which
10. customThe liquors were decanted from the resultant white crystals which
11. customwere then dried in vacuo

ORD record

ord-131a35b24d0a4e8c87088cb01865a3f6

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249160B2