4-Iodobenzoic acid → 4-Iodobenzoyl chloride

HRID 849891Notes

Reaction equation

HRID 849891 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][CH:3]=1.S(Cl)([Cl:13])=O>C(Cl)(Cl)Cl.CN(C)C=O>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:13])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 120854-Iodobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 743734-Iodobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent2×

Procedure

A round bottom flask was charged with 4-iodobenzoic acid (3.0 g, 12.1 mmol) in chloroform (100 mL). To the solution was added thionyl chloride (5.0 mL) in chloroform (10 mL) and 2-3 drops of dimethylformamide (DMF). The slurry was heated at reflux for 2 hours. while monitoring the reaction through an oil bubbler. A clear solution of 4-iodobenzoyl chloride was obtained. The volatiles were removed and a colorless oil was obtained which solidified upon cooling.

Workup

  1. temperatureThe slurry was heated
  2. temperatureat reflux for 2 hours
  3. customthe reaction through an oil bubbler

Sources & evidence

ORD record
ord-b02c4e66d2dd49d39495a9a2703e1e08
Source dataset
uspto-grants-2000_01
Patent number
US06015543

Reaction notes

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