Boron tribromide → 3-Bromo-4-fluorobenzyl Bromide

(3-Bromo-4-fluorophenyl)methanol (0.264 g, 1.29 mmol) was dissolved in DCM (3 mL). The solution was cooled to 0 deg, and tribromoborane (1.0 M in DCM, 0.863 ml, 0.863 mmol) was added. The mixture was stirred at 0 deg for 1 h, then rt for 1 h. The reaction was quenched with water, and the mixture was transferred to a separatory funnel with half-saturated NaHCO3 (15 mL), and the aqueous phase was extracted with DCM (3×20 mL). The organics were combined, washed with half-saturated brine (5 mL), dried over sodium sulfate and concentrated. Purification of the residue through silica gel (40 mL) using 5% EtOAc-hexane afforded the title compound.

1. temperatureThe solution was cooled to 0 deg
2. waitrt for 1 h
3. customThe reaction was quenched with water
4. customthe mixture was transferred to a separatory funnel with half-saturated NaHCO3 (15 mL)
5. extractionthe aqueous phase was extracted with DCM (3×20 mL)
6. washwashed with half-saturated brine (5 mL)
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated
9. customPurification of the residue through silica gel (40 mL)

ORD record

ord-bdee873a287547a4bb709c42021939a4

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07745484B2