Thionyl Chloride → 2,3,4-Trichloro-5-fluorobenzoyl chloride

Reaction equation

[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]([Cl:12])[C:8]([F:13])=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:16])=O>>[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]([Cl:12])[C:8]([F:13])=[CH:7][C:3]=1[C:4]([Cl:16])=[O:5]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 141498672,3,4-Trichloro-5-fluorobenzoic acid

Product 1

HCID 141498692,3,4-Trichloro-5-fluorobenzoyl chloride

Procedure

737 g (3.02 mols) of 2,3,4-trichloro-5-fluorobenzoic acid are introduced into 1.5 liters of thionyl chloride at room temperature, and the mixture is refluxed for 16 hours until the gas evolution ceases. Excess thionyl chloride is removed by distillation, and the residue is distilled.

Workup

temperaturethe mixture is refluxed for 16 hours until the gas evolution ceases
customExcess thionyl chloride is removed by distillation
distillationthe residue is distilled

Sources & evidence

ORD record: ord-3fbc7edb034d43bf846303d406b61176
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04851160

Reaction notes

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