Acetyl chloride → Methyl 2-(4-bromophenyl)acetate

HRID 553288Notes

Reaction equation

HRID 553288 reaction equation
[C:1](Cl)(=O)C.[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[CH:8][CH:7]=1>CO>[CH3:1][O:14][C:13](=[O:15])[CH2:12][C:9]1[CH:8]=[CH:7][C:6]([Br:5])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 316783Methyl 2-(4-bromophenyl)acetateYield 100.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetyl chloride (10 g) was added dropwise over 5 minutes to methanol (250 mL). After 5 minutes, (4-bromo-phenyl)-acetic acid (15 g) was added. The resulting mixture was stirred for 96 hours, concentrated and the residue azeotroped with toluene (×2) to give the subtitle compound as a yellow oil (16 g).

Workup

  1. concentrationconcentrated
  2. customthe residue azeotroped with toluene (×2)

Sources & evidence

ORD record
ord-b04f42c4a6c243de99ce225f456714d3
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Reaction notes

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