Dimethylformamide → 2-Chloro-4-iodobenzoyl chloride

HRID 963397Notes

Reaction equation

HRID 963397 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:14])=O.CN(C)C=O>C1C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4]([Cl:14])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 8212642-Chloro-4-iodobenzoic Acid

Product 1

HCID 190815362-Chloro-4-iodobenzoyl chlorideYield 74%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A suspension of 66 g of 2-chloro-4-iodo-benzoic acid (I.G.Farbenind. D.R.P. 565411 1930) in 690 ml of benzene is treated at 4° C. with 20.56 ml of thionyl chloride and 0.1 ml of dimethylformamide and the mixture is boiled at reflux under argon for 21 hrs. The reaction mixture is concentrated. Distillation of the residue at 160°/60 Pa yields 51.9 g (74%) of 2-chloro-4-iodo-benzoyl chloride as a colourless liquid.

Workup

  1. temperatureat reflux under argon for 21 hrs
  2. concentrationThe reaction mixture is concentrated
  3. distillationDistillation of the residue at 160°/60 Pa

Sources & evidence

ORD record
ord-911a5d42828e4e5eb8049b1af7dabb18
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

Loading…