2-Iodobenzoic acid → 2-Iodobenzoyl chloride

HRID 1012345Notes

Reaction equation

HRID 1012345 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:14])=O>C(Cl)(Cl)Cl.CN(C)C=O>[I:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:14])=[O:5]

Participants

5

Reactant 2

HCID 69412-Iodobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 691122-Iodobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 2-iodobenzoic acid (5.00 g, 20.1 mmol) in chloroform (50 ml) were added oxalyl chloride (1.9 ml, 21.7 mmol) and N,N-dimethylformamide (5 drops with Pasteur pipette) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure and ethyl acetate (5 ml) was added to the residue to give a solution of 2-iodobenzoyl chloride in ethyl acetate.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure and ethyl acetate (5 ml)
  3. additionwas added to the residue

Sources & evidence

ORD record
ord-a89d44fdbede4018972c59223125d324
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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