Thionyl Chloride → 3-Difluoromethoxy-2,4,5-trifluoro-6-nitrobenzoyl chloride

HRID 1440100Notes

Reaction equation

HRID 1440100 reaction equation
S(Cl)([Cl:3])=O.[F:5][CH:6]([F:23])[O:7][C:8]1[C:9]([F:22])=[C:10]([C:14]([N+:19]([O-:21])=[O:20])=[C:15]([F:18])[C:16]=1[F:17])[C:11](O)=[O:12]>C1C=CC=CC=1>[F:5][CH:6]([F:23])[O:7][C:8]1[C:9]([F:22])=[C:10]([C:14]([N+:19]([O-:21])=[O:20])=[C:15]([F:18])[C:16]=1[F:17])[C:11]([Cl:3])=[O:12]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 150238363-(Difluoromethoxy)-2,4,5-trifluoro-6-nitrobenzoic acid

Product 1

HCID 150238423-Difluoromethoxy-2,4,5-trifluoro-6-nitrobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

40 ml of thionyl chloride were added to a solution of 15.97 g (0.056 moles) of 3-difluoromethoxy-2,4,5-trifluoro-6-nitrobenzoic acid [(XII), R1 =--OCHF2, R3' =NO2, X=X'=F] in 50 ml of benzene, and the mixture was heated under reflux for 2 hours. At the end of this time, the benzene and the excess thionyl chloride were removed by distillation under reduced pressure to give 16.50 g of 3-difluoromethoxy-2,4,5-trifluoro-6-nitrobenzoyl chloride [(XIII), R1 =--OCHF2, R3' =NO2, X=X'=F].

Workup

  1. temperatureunder reflux for 2 hours
  2. customAt the end of this time, the benzene and the excess thionyl chloride were removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-26adc1dc920e49baac13270d1e4fcbf5
Source dataset
uspto-grants-1996_03
Patent number
US05496951

Reaction notes

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