Oxalyl chloride → 4-Bromo-2-methylbenzoyl chloride

HRID 378894Notes

Reaction equation

HRID 378894 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>[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

4

Reactant 2

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

Product 1

HCID 128464834-Bromo-2-methylbenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneCatalyst

Procedure

A suspension of 4bromo-2-methylbenzoic acid (4.9 g, 22.8 mmol) in dichioromethane containing a few drops of N,N-dimethylformamde 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-b5ef46d355a645e1ae379e14e4216879
Source dataset
uspto-grants-2001_10
Patent number
US06297234B1

Reaction notes

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