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

HRID 1985984Notes

Reaction equation

HRID 1985984 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 re-dissolved in dichloromethane, dried over sodium sulfate and concentrated in vacuo to give the title compound as a colourless oil (20.6 g). 1H NMR (400 MHz, CDCl3): δ: 3.59 (2H, s), 3.70 (3H, s), 7.17-7.24 (2H, m), 7.37-7.45 (2H, m); LRMS ESI m/z 253 [M+Na]+

Workup

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

Sources & evidence

ORD record
ord-998a405a9cfb4d9ab0e2e7a915bfd4cc
Source dataset
uspto-grants-2009_06
Patent number
US07547731B2

Reaction notes

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