Oxalyl chloride → 3-Chloro-5-fluorobenzoyl chloride

HRID 431887Notes

Reaction equation

HRID 431887 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[C:5](O)=[O:6].C(Cl)(=O)C([Cl:15])=O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[C:5]([Cl:15])=[O:6]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 27348403-Chloro-5-fluorobenzoic acid

Product 1

HCID 38491553-Chloro-5-fluorobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Chloro-5-fluorobenzoic acid (400 mg, 2.3 mmol) was treated with a solution of oxalyl chloride (4.6 mL of 2.5 M in dichloromethane, 11.5 mmol) and a catalytic amount of N,N-dimethylformamide. The reaction was stirred at ambient temperature for 2.5 hours. The excess oxalyl chloride was removed in vacuo to afford 3-chloro-5-fluorobenzoyl chloride.

Workup

  1. customThe excess oxalyl chloride was removed in vacuo

Sources & evidence

ORD record
ord-8f6ce96f1c5f4d9f8f86a30e835e1462
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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