Acetyl chloride → Methyl 3-bromo-4-chlorobenzoate

HRID 1848603Notes

Reaction equation

HRID 1848603 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-c85fe5022169442db8693ea5bf6bbc7b
Source dataset
uspto-grants-2015_02
Patent number
US08952161B2

Reaction notes

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