3-Iodobenzoic acid → 3-Iodobenzoyl chloride

HRID 1291093Notes

Reaction equation

HRID 1291093 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].S(Cl)([Cl:13])=O>>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([Cl:13])=[O:6]

Participants

3

Reactant 2

HCID 120603-Iodobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 743783-Iodobenzoyl chlorideYield 67%

Procedure

2.21 g (0.00891 mol) of 3-iodobenzoic acid were dissolved in 25 ml of thionyl chloride under argon and boiled under reflux for 2 hrs. The excess thionyl chloride was distilled off and the residue was taken up twice with 50 ml of toluene and concentrated each time. 1.6 g (67%) of 3-iodobenzoyl chloride were obtained as a yellow solid.

Workup

  1. temperatureunder reflux for 2 hrs
  2. distillationThe excess thionyl chloride was distilled off
  3. concentrationconcentrated each time

Sources & evidence

ORD record
ord-aa9b59ca133a4e2587146771eb1e8260
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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