Reaction #607440

Reaction equation

3′,5′-difluoroacetophenone

sodium borohydride

→

title compound

Yield 99.3%

1-(3,5-difluorophenyl)ethanol

Yield 99.3%

Solvents

methanol

Conditions

Workup

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

Procedure

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.

Source