Acetyl chloride → Methyl 3-bromo-4-chlorobenzoate

HRID 661643Notes

Reaction equation

HRID 661643 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([OH:7])=[O:6].[C:12](Cl)(=O)C>CO>[CH3:12][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([Cl:11])=[C:2]([Br:1])[CH:3]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 27355443-Bromo-4-chlorobenzoic acid

Product 1

HCID 22352523Methyl 3-bromo-4-chlorobenzoateYield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 3-bromo-4-chloro-benzoic acid (10 g, 42.6 mmol) in MeOH (100 mL) cooled with ice bath, was added acetyl chloride (30.4 mL, 0.43 mol) dropwise. The mixture was then stirred at room temperature for 12 hrs and concentrated to yield 3-bromo-4-chloro-benzoic acid methyl ester as a yellow solid (10.6 g). NMR (CDCl3), 6, 8.28 (1H, s), 7.91 (1H, brs), 7.52 (1H, brs), 3.92 (3H, s).

Workup

  1. temperaturecooled with ice bath
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-12f4d011e2f9426abc0d349decf59e6c
Source dataset
uspto-grants-2011_12
Patent number
US08084614B2

Reaction notes

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