Sodium borohydride → [4-Bromo-2-(trifluoromethoxy)phenyl]methanol

Temperature

0 °C

To a stirred solution of 4-bromo-2-(trifluoromethoxy)benzaldehyde (5.0 g, 19 mmol) from Step 1 above in EtOH (100 mL) at 0° C. was added NaBH4 (0.88 g, 23 mmol). The mixture was stirred for 1 h at 0° C., the cooling bath was removed, and the solution was stirred at ambient temperature for 14 h. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc (150 mL) and saturated aqueous NaHCO3 (75 mL). The organic phase was separated, dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using a gradient elution of 5-10% EtOAc:hexanes. 4-Bromo-2-(trifluoromethoxy)benzyl alcohol was obtained as an amorphous solid by evaporation from CH2Cl2 (TLC Rf =0.25 (10% EtOAc:hexanes); HPLC retention time=8.8 min (method A)).

1. customthe cooling bath was removed
2. stirringthe solution was stirred at ambient temperature for 14 h
3. customThe solvent was removed under reduced pressure
4. customthe residue was partitioned between EtOAc (150 mL) and saturated aqueous NaHCO3 (75 mL)
5. customThe organic phase was separated
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. customthe solvent was removed under reduced pressure
9. customThe residue was purified by pressurized silica gel column chromatography
10. washa gradient elution of 5-10% EtOAc

ORD record

ord-2432fbcaa1f445c28eea25e9c63f7321

Source dataset

uspto-grants-2000_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06090805