Dimethylformamide → 2-Bromo-5-methoxybenzoyl chloride

HRID 431894Notes

Reaction equation

HRID 431894 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:16])=O.CN(C)C=O>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([Cl:16])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 899062-Bromo-5-methoxybenzoic acid

Product 1

HCID 27816562-Bromo-5-methoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Bromo-5-methoxybenzoic acid (231 mg, 1.0 mmol) in dichloromethane (1.5 mL) was treated with a solution of oxalyl chloride (1.5 mL of 2 M in dichloromethane, 3 mmol) and a catalytic amount of N,N-dimethylformamide. The reaction was stirred overnight at ambient temperature. The excess oxalyl chloride was removed in vacuo to afford 2-bromo-5-methoxybenzoyl chloride.

Workup

  1. customThe excess oxalyl chloride was removed in vacuo

Sources & evidence

ORD record
ord-c785b66feaab41fb9a248ffe8cc1756c
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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