Reaction #674288

Reaction equation

NH4Cl

NaBH4

2′,6′-dichloro-5′-fluoroacetophenone

NaBH4

→

(±)1-(2,6-dichloro-3-fluorophenyl)ethanol

Yield 105.2%

Solvents

MeOH

Conditions

Workup

1. 1
   Temperatureto warm to room temperature
2. 2
   workup.STIRRINGstirred at room temperature for 30 min
3. 3
   ConcentrationThe reaction solution was concentrated
4. 4
   Otherto remove the solvent
5. 5
   Otherto give the residue
6. 6
   ExtractionThe aqueous phase was then extracted with EtOAc (3×65 mL)
7. 7
   WashThe combined organic phase was washed with H2O (50 mL) and brine (50 mL)
8. 8
   Dryingdried over anhydrous Na2SO4
9. 9
   Concentrationconcentrated by evaporation in vacuo

Procedure

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.

Source