4-Bromo-2-fluorobenzaldehyde → (4-Bromo-2-fluorophenyl)methanol

To a stirred solution of 4-Bromo-2-fluoro benzaldehyde (15 g, 79.36 mmol) in MeOH (100 mL) at −5° C. to 0° C. was added NaBH4 (6.0 g, 158.73 mmol) in equal portions and stirred at RT for 1 h until the starting material was completely consumed, as evidenced by TLC analysis. The reaction mixture was then diluted with ice cold water (100 mL) and concentrated under reduced pressure. The residue obtained on concentration was extracted with EtOAc (2×200 mL) and separated. The combined EtOAc layers were washed with brine solution (50 mL), dried over anhydrous NaSO4, filtered and concentrated to afford (4-bromo-2-fluorophenyl)methanol (30 g, 99% (from 2 batches))] as colorless oil (TLC solvent system: 30% EtOAc in PE; Rf: 0.3).

1. customwas completely consumed
2. additionThe reaction mixture was then diluted with ice cold water (100 mL)
3. concentrationconcentrated under reduced pressure
4. customThe residue obtained on concentration
5. extractionwas extracted with EtOAc (2×200 mL)
6. customseparated
7. washThe combined EtOAc layers were washed with brine solution (50 mL)
8. dry with materialdried over anhydrous NaSO4
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-487a41463a8547b782675b8464a15288

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946204B2