Acetyl chloride → Methyl 2-(3-bromophenyl)acetate

HRID 916072Notes

Reaction equation

HRID 916072 reaction equation
[C:1](Cl)(=O)C.[Br:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([OH:15])=[O:14])[CH:9]=[CH:10][CH:11]=1>CO>[CH3:1][O:14][C:13](=[O:15])[CH2:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([Br:5])[CH:7]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 74653(3-Bromophenyl)acetic acid

Product 1

HCID 11746402Methyl 2-(3-bromophenyl)acetateYield 967%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetyl chloride (0.70 ml, 9.30 mmol) was slowly added to a solution of (3-bromo-phenyl)-acetic acid (20.0 g, 93 mmol) in methanol (500 ml) at 0° C. under nitrogen and the reaction was allowed to warm gradually to room temperature over a period of 5 hours. The solvent was removed in vacuo and the residual oil was dissolved in dichloromethane, dried (sodium sulfate) and concentrated in vacuo to give the title compound as a colourless oil (20.6 g).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residual oil was dissolved in dichloromethane
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8591c7591e5b47918b8338512a687a85
Source dataset
uspto-grants-2007_09
Patent number
US07268147B2

Reaction notes

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