Oxalyl chloride → 4-Bromo-2-methylbenzoyl chloride

HRID 1387307Notes

Reaction equation

HRID 1387307 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([CH3:11])[CH:3]=1.C(Cl)(=O)C([Cl:15])=O>ClCCl.CN(C)C=O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:15])=[O:7])=[C:4]([CH3:11])[CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 128464834-Bromo-2-methylbenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneCatalystHCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-bromo-2-methylbenzoic acid (4.9 g, 22.8 mmol) in dichloromethane containing a few drops of N,N-dimethylformamide was treated dropwise under nitrogen with oxalyl chloride (2.4 mL, 27.5 mol). After gas evolution subsided, the reaction mixture was refluxed for an additional 15 minutes and then evaporated to dryness in vacuo to provide the crude 4-bromo-2-methylbenzoyl chloride.

Workup

  1. temperaturethe reaction mixture was refluxed for an additional 15 minutes
  2. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-5dccd09901b84d3eb34b96fc57827b34
Source dataset
uspto-grants-2001_07
Patent number
US06268360B1

Reaction notes

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