Thionyl Chloride → 3-Fluoro-2-methylbenzoyl chloride

Reaction equation

[F:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].S(Cl)([Cl:14])=O>>[F:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([Cl:14])=[O:6]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 2466823-Fluoro-2-methylbenzoic acid

Product 1

HCID 27792403-Fluoro-2-methylbenzoyl chloride

Procedure

A solution of 2.87 g of 3-fluoro-2-methylbenzoic acid in 25 ml of thionyl chloride is refluxed for 1.75 hour and the excess thionyl chloride removed under vacuum. To the residue is added toluene (several times) and the toluene removed under vacuum after each addition to give 3-fluoro-2-methylbenzoyl chloride.

Workup

customthe excess thionyl chloride removed under vacuum
additionTo the residue is added toluene (several times)
customthe toluene removed under vacuum
additionafter each addition

Sources & evidence

ORD record: ord-68580e8b0b3e49b7b5833ece3c1c71da
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05624923

Reaction notes

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