1-(4-Bromophenyl)propan-2-one → 1-(4-Bromophenyl)propan-2-ol

HRID 735700Notes

Reaction equation

HRID 735700 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH:9]([OH:11])[CH3:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7363321-(4-Bromophenyl)propan-2-oneHCID 4311764Sodium borohydride

Product 1

HCID 198829011-(4-Bromophenyl)propan-2-olYield 96.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-bromophenylacetone (5.00 g, 23.5 mmol) in ethanol (100 mL) at 0° C., was added sodium borohydride (976 mg, 25.8 mmol) portionwise over 5 min. The mixture was stirred at rt for 15 h, then quenched with 5% citric acid. The volatile solvent was removed in vacuo. The mixture was diluted with water, the pH was adjusted to 4.5 with 1N HCl, then aqueous phase was extracted with CH2Cl2 (3×). The combined organic washed with brine, dried (Na2SO4), filtered through a pad of SiO2 (eluted with 10% EtOAc/CH2Cl2) and concentrated to afford 4.90 g of 77A as a colorless oil. MS (ESI) m/z 197.1 (M-OH)+.

Workup

  1. customquenched with 5% citric acid
  2. customThe volatile solvent was removed in vacuo
  3. additionThe mixture was diluted with water
  4. extractionaqueous phase was extracted with CH2Cl2 (3×)
  5. washThe combined organic washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered through a pad of SiO2 (eluted with 10% EtOAc/CH2Cl2)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-26d3f76f7853431ca54b6881610a6e64
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

Loading…