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 r.t. for 1 h. under nitrogen. The solution was cooled in an ice bath and 125 ml of methanol was then added slowly. The solvents were 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 layer was 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 solvents were 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 layer was dried with sodium sulfate
6. customThe solvent was removed

ORD record

ord-a56f1d545b2248d7a1439d9d43519eeb

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06448429B1