4-Iodobenzoic acid → 4-Iodobenzoyl chloride

HRID 1427732Notes

Reaction equation

HRID 1427732 reaction equation
S(Cl)([Cl:3])=O.[I:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](O)=[O:11])=[CH:8][CH:7]=1>C(Cl)Cl.CN(C=O)C>[I:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([Cl:3])=[O:11])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 120854-Iodobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 743734-Iodobenzoyl chlorideYield 96%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (36.0 g, 302 mmol) was added to a suspension of 4-iodobenzoic acid (50.0 g, 202 mmol) in anhydrous DCM (300 ml) followed by a few drops of DMF and the reaction mixture was stirred overnight at r.t. Upon completion, reaction flask was concentrated under reduced pressure to yield 51.6 g (96.0% yield) of crude 4-iodobenzoyl chloride that was used in the next step without further purification.

Workup

  1. customUpon completion, reaction flask
  2. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-a17d209acf1b48f5a511fc0519a9809d
Source dataset
uspto-grants-2015_01
Patent number
US08933261B2

Reaction notes

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