Oxalyl chloride → 4-Chloro-2-iodobenzoyl chloride

HRID 1868878Notes

Reaction equation

HRID 1868878 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([I:11])[CH:3]=1.C(Cl)(=O)C([Cl:15])=O>CN(C=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:15])=[O:7])=[C:4]([I:11])[CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 1394524-Chloro-2-iodobenzoic acid

Product 1

HCID 218675214-Chloro-2-iodobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A catalytic amount of DMF (approximately 3 drops) was added to a stirred mixture of 4-chloro-2-iodobenzoic acid (24.47 g, 86.63 mmol) and oxalyl chloride (11.34 mL, 129.9 mmol) in DCM (100 mL) under a nitrogen atmosphere. The reaction mixture was stirred for 2 hours and then concentrated in vacuo to give 4-chloro-2-iodobenzoyl chloride as a yellow oil that solidified upon standing (26.07 g).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-731255f1af4b44248dce4079b782a84c
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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