Sodium borohydride → (2-Bromo-4-chlorophenyl)methanol

A solution of 2-bromo-4-chlorobenzaldehyde (21.95 g; 100.0 mmol) in 200 mL methanol was stirred and cooled in an ice bath for 15 minutes, and solid sodium borohydride (1.9 g; 50.0 mmol) was added. A yellow color formed and there was copious gas evolution. Stirring was continued in the bath for 1 hour. The solution was diluted with 200 mL water, and then the methanol was evaporated on a rotary evaporator. The residual mixture was extracted with 200 mL EtOAc. The organic layer was washed with 50 mL brine, then dried over sodium sulfate and evaporated. The residual solid was washed out of the flask with hexane and collected by filtration, ground with a mortar and pestle to break up the chunks, then washed with hexane and air-dried on the filter to give 17.8 g of (2-bromo-4-chlorophenyl)methanol as a white solid.

1. temperaturecooled in an ice bath for 15 minutes
2. customA yellow color formed
3. customthe methanol was evaporated on a rotary evaporator
4. extractionThe residual mixture was extracted with 200 mL EtOAc
5. washThe organic layer was washed with 50 mL brine
6. dry with materialdried over sodium sulfate
7. customevaporated
8. washThe residual solid was washed out of the flask with hexane
9. filtrationcollected by filtration, ground with a mortar and pestle
10. washwashed with hexane
11. customair-dried on the
12. filtrationfilter

ORD record

ord-da0fda51d24e49b180299ac4ffa81015

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08716498B2