Thionyl Chloride → o-Iodophenylacetyl chloride

HRID 1457623Notes

Reaction equation

HRID 1457623 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=O.S(Cl)([Cl:14])=O>>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([Cl:14])=[O:11]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 27800902-Iodophenylacetic acid

Product 1

HCID 10934858o-Iodophenylacetyl chloride

Procedure

A solution of 13.32 g (0.05 mol) of 2-iodophenylacetic acid in 75 ml thionyl chloride is refluxed for 2 hours, and the volatiles removed under vacuum. Toluene is added (3 times) and the solvent removed under vacuum after each addition to give 2-iodophenylacetyl chloride as a gum. To the preceding compound (0.05 mol) in a mixture of 100 ml of toluene-dichloromethane (1:1) is added 11 g (0.05 mol) of 2-iodoaniline and (0.10 mol) of diisopropylethylamine.

Workup

  1. customthe volatiles removed under vacuum
  2. additionToluene is added (3 times)
  3. customthe solvent removed under vacuum
  4. additionafter each addition

Sources & evidence

ORD record
ord-f22fda3f6bc3499090d561c91440aca6
Source dataset
uspto-grants-1998_12
Patent number
US05849735

Reaction notes

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