Thionyl Chloride → 3-Bromo-4-fluorobenzonitrile

HRID 851287Notes

Reaction equation

HRID 851287 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([NH2:7])=O.S(Cl)(Cl)=O>>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]#[N:7]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 27733293-Bromo-4-fluorobenzamide

Product 1

HCID 1235793-Bromo-4-fluorobenzonitrileYield 91%

Procedure

765 g (3.5 moles) of 3-bromo-4-fluoro-benzoic acid amide was added, at 25° C., to 1,150 g (9.7 moles) of thionyl chloride and the mixture was heated under reflux at 85° to 90° C., while stirring, until virtually no further evolution of gas took place. The excess thionyl chloride was then distilled off and the residue was fractionated in a short column. 630 g (91% of theory) of 3-bromo-4-fluoro-benzonitrile with a boiling point of 115°-116° C./20 mm Hg were obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux at 85° to 90° C.
  3. distillationThe excess thionyl chloride was then distilled off

Sources & evidence

ORD record
ord-389ca1d4043b4210994934deab942952
Source dataset
uspto-grants-1983_05
Patent number
US04383949

Reaction notes

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