Methanol → [2-Bromo-4-(bromomethyl)phenyl]methanol

The compound of Step 1 (23.8 g, 81 mmol, 1 eq) was dissolved in THF under nitrogen at 0° C. A 1M borane solution in THF (242 ml, 242 mmol, 3 eq) was then added dropwise and the mixture was stirred at RT for 1 hour under nitrogen. The solution was cooled in an ice bath and 125 ml of methanol was then added slowly. The solvent was removed and the mixture partitioned between 400 ml of water and 400 ml of 20% THF/EtOAc. The aqueous layer was washed 3 times with 400 ml of 20% THF/EtOAc and the combined organic layers were dried with sodium sulfate. The solvent was removed and 19.7 g (87%) of the title compound was obtained.

1. temperatureThe solution was cooled in an ice bath
2. customThe solvent was removed
3. customthe mixture partitioned between 400 ml of water and 400 ml of 20% THF/EtOAc
4. washThe aqueous layer was washed 3 times with 400 ml of 20% THF/EtOAc
5. dry with materialthe combined organic layers were dried with sodium sulfate
6. customThe solvent was removed

ORD record

ord-455ba49a7fad42dca6c47ac7c6fb92c8

Source dataset

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06583126B2