Methanol → Methyl 2-(4-bromophenyl)acetate

HRID 55295Notes

Reaction equation

HRID 55295 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH3:12]O>>[CH3:12][O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 316783Methyl 2-(4-bromophenyl)acetate

Procedure

A solution of 100 g of 4-bromophenylacetic acid in 1.5 l of methanol is mixed with 232 g of Amberlyst 15, and the suspension is stirred for 48 hours at room temperature. The reaction mixture is suctioned off on diatomaceous earth, the filter residue is washed with dichloromethane, and the filtrate is concentrated by evaporation. The residue is taken up in ethyl acetate, washed with 10% sodium bicarbonate solution and saturated common salt solution, dried on sodium sulfate and concentrated by evaporation. 106 g of 4-bromophenylacetic acid methyl ester is obtained as oil.

Workup

  1. washthe filter residue is washed with dichloromethane
  2. concentrationthe filtrate is concentrated by evaporation
  3. washwashed with 10% sodium bicarbonate solution and saturated common salt solution
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-685cd69b188c4f41905437882c80882f
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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