1-(3-Bromo-4-fluorophenyl)ethan-1-one → 1-(3-Bromo-4-fluorophenyl)ethanol

HRID 1259295Notes

Reaction equation

HRID 1259295 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[F:8].[BH4-].[Na+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 705081-(3-Bromo-4-fluorophenyl)ethan-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 207853061-(3-Bromo-4-fluorophenyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(3-bromo-4-fluorophenyl)ethanone (15.0 g, 69 mmol) in tetrahydrofuran (200 mL) was treated with sodium borohydride (5.3 g, 138 mmol) at 0° C. After the addition, the ice bath was removed, and the mixture was stirred at room temperature for 30 minutes and at reflux overnight. After cooling, 1N HCl (10 mL) was slowly added and the reaction mixture was concentrated. The residue was partitioned between ethyl acetate and brine. The organic phase was washed with water, and concentrated. The residue was purified by flash chromatography (30% ethyl acetate in hexane) to provide the title compound. MS (DCI/NH3) m/z 220 (M+H)+.

Workup

  1. additionAfter the addition
  2. customthe ice bath was removed
  3. temperatureat reflux overnight
  4. temperatureAfter cooling
  5. addition1N HCl (10 mL) was slowly added
  6. concentrationthe reaction mixture was concentrated
  7. customThe residue was partitioned between ethyl acetate and brine
  8. washThe organic phase was washed with water
  9. concentrationconcentrated
  10. customThe residue was purified by flash chromatography (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-17f818d0fe3f4d93a8a48433303b2303
Source dataset
uspto-grants-2013_06
Patent number
US08466150B2

Reaction notes

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