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

HRID 494425Notes

Reaction equation

HRID 494425 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>[Br:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([O:15][CH3:1])=[O:14])[CH:9]=[CH:10][CH:11]=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 (0.7 mL, 9.3 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 redissolved 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 redissolved in dichloromethane
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-916ddf591aa34dd9ad03d81ef7aff9b3
Source dataset
uspto-grants-2009_05
Patent number
US07538141B2

Reaction notes

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