Acetyl chloride → Methyl 3-bromo-4-chlorobenzoate

HRID 1485958Notes

Reaction equation

HRID 1485958 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), δ, 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-7045f1b810ee45f78c6fc3bc80cd0dfd
Source dataset
uspto-grants-2016_08
Patent number
US09422310B2

Reaction notes

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