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

HRID 365325Notes

Reaction equation

HRID 365325 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 (11.05 g).

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-96b1c52b41ef42a59bdca00f24fafa21
Source dataset
uspto-grants-2000_10
Patent number
US06127361

Reaction notes

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