2,3,5-Triiodobenzoic acid → 2,3,5-Triiodobenzoyl chloride

HRID 375030

Reaction equation

HRID 375030 reaction equation
[I:1][C:2]1[C:10]([I:11])=[CH:9][C:8]([I:12])=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:16])=O>ClCCl.CN(C=O)C.C1(C)C=CC=CC=1>[I:1][C:2]1[C:10]([I:11])=[CH:9][C:8]([I:12])=[CH:7][C:3]=1[C:4]([Cl:16])=[O:5]

Participants

6

Reactant 2

HCID 69482,3,5-Triiodobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 27608062,3,5-Triiodobenzoyl chloride

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 15.0 g (30.0 mmol) of 2,3,5-triiodobenzoic acid and 19.0 g (150 mmol) of oxalyl chloride in 60 ml of dry dichloromethane was placed under nitrogen and cooled to 0° C. Two drops of dry DMF were added, the ice bath was removed and the resulting suspension was stirred at room temperature for 1.5 hrs. The resulting brown solution was concentrated in vacuo to produce a tan solid. The solid was dissolved in 30 ml of dry toluene and was concentrated in vacuo. The toluene concentration was repeated two more times to yield 2,3,5-triiodobenzoyl chloride as a tan solid.

Workup

  1. customthe ice bath was removed
  2. concentrationThe resulting brown solution was concentrated in vacuo
  3. customto produce a tan solid
  4. concentrationwas concentrated in vacuo
  5. concentrationThe toluene concentration

Sources & evidence

ORD record
ord-1597f145b8304576ab4ccfc670b2f5fc
Source dataset
uspto-grants-1996_01
Patent number
US05484585

Linked notes

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