Ammonium Chloride → 1-(2,6-Dichloro-3-fluorophenyl)ethan-1-ol

Temperature

0 °C

To a solution of 2′,6′-dichloro-5′-fluoroacetophenone (10.4 g, 50 mmol) in MeOH (anhydrous, 80 mL) was added NaBH4 (3.78 g, 100 mmol) in portions at 0° C. After the addition of NaBH4, the solution was stirred at 0° C. for 10 min, then allowed to warm to room temperature and stirred at room temperature for 30 min. The reaction solution was concentrated to remove the solvent to give the residue. A saturated solution of NH4Cl (60 mL) was added slowly. The aqueous phase was then extracted with EtOAc (3×65 mL). The combined organic phase was washed with H2O (50 mL) and brine (50 mL), dried over anhydrous Na2SO4, concentrated by evaporation in vacuo to afford (±)1-(2,6-dichloro-3-fluorophenyl)ethanol (11 g, 100%) as a colorless oil.

1. temperatureto warm to room temperature
2. stirringstirred at room temperature for 30 min
3. concentrationThe reaction solution was concentrated
4. customto remove the solvent
5. customto give the residue
6. extractionThe aqueous phase was then extracted with EtOAc (3×65 mL)
7. washThe combined organic phase was washed with H2O (50 mL) and brine (50 mL)
8. dry with materialdried over anhydrous Na2SO4
9. concentrationconcentrated by evaporation in vacuo

ORD record

ord-b209ca1998d24726b377f015c5e648c6

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09226923B2