Bromomethyl 4-methoxyphenyl ketone → 2-Bromo-1-(4-methoxyphenyl)ethan-1-ol

HRID 2304399Notes

Reaction equation

HRID 2304399 reaction equation
[BH4-].[Na+].[Br:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:6]>CO>[Br:3][CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)[OH:6]

Participants

4

Reactant 2

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 4311764Sodium borohydride

Product 1

HCID 142885062-Bromo-1-(4-methoxyphenyl)ethan-1-olYield 109.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.826 g (21.8 mmol) of sodium borohydride was added to 2-bromo-4′-methoxy-acetophenone (10 g, 43.7 mmol) in methanol (200 ml) and the mixture was stirred for 1 hour at room temperature. The mixture was concentrated in vacuo and saturated aqueous sodium chloride was added to the residue and the product was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give 2-bromo-1-(4′-methoxyphenyl) ethanol (11.05g).

Workup

  1. concentrationThe mixture was concentrated in vacuo and saturated aqueous sodium chloride
  2. additionwas added to the residue
  3. extractionthe product was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cb65006880f048a69305844550d0db78
Source dataset
uspto-grants-2002_08
Patent number
US06436922B1

Reaction notes

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