Reaktion #607440

ord-15b6b7f4129b4f74952914e02c45668f

Reaktionsgleichung

CC(=O)c1cc(F)cc(F)c1
3′,5′-difluoroacetophenone
[BH4-].[Na+]
sodium borohydride
CC(O)c1cc(F)cc(F)c1
title compound
Ausbeute 99.3%
CC(O)c1cc(F)cc(F)c1
1-(3,5-difluorophenyl)ethanol
Ausbeute 99.3%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigequenched carefully by the addition of a saturated aqueous ammonium chloride solution (150 mL)
  2. 2
    ExtraktionThe extraction
  3. 3
    WaschenThe combined organic layers were washed with brine (200 mL)
  4. 4
    Trocknendried over anhydrous Na2SO4
  5. 5
    Filtrationfiltered
  6. 6
    SonstigeThe solvent was removed in vacuo

Vorschrift

To a colorless stirred solution of 3′,5′-difluoroacetophenone (50.00 g, 320.24 mmol) in methanol (320 mL), sodium borohydride (3.41 g, 86.47 mmol, 0.27 eq) was added portion wise over 20 minutes at room temperature under inert atmosphere (Ar). Then the reaction mixture was stirred for 45 min at room temperature and then quenched carefully by the addition of a saturated aqueous ammonium chloride solution (150 mL). The extraction was carried out with ethyl acetate (2×200 mL). The combined organic layers were washed with brine (200 mL), dried over anhydrous Na2SO4 and filtered. The solvent was removed in vacuo to give the title compound (50.29 g, 99%) as a colorless oil. The alcohol was used as such in the subsequent step.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09326513B2uspto-grants-2016_05