Acrylonitrile → 3-[4-Chloro-2-(2-fluorobenzoyl)phenyl]prop-2-enenitrile

HRID 1995550Notes

Reaction equation

HRID 1995550 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH:16]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[F:15])=[O:8].C(N(CC)CC)C.[C:25](#[N:28])[CH:26]=[CH2:27]>Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:7]([C:6]1[CH:16]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[CH:27]=[CH:26][C:25]#[N:28])=[O:8]

Participants

6

Reactant 3

HCID 7855AcrylonitrileHCID 8471TriethylamineHCID 12948263(5-Chloro-2-iodophenyl)(2-fluorophenyl)methanone

Product 1

HCID 539727423-[4-Chloro-2-(2-fluorobenzoyl)phenyl]prop-2-enenitrile

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 313Hydrochloric AcidSolvent

Procedure

A solution of 5.0 g (14 mmol) of 5-chloro-2'-fluoro-2-iodobenzophenone, 2 ml (14.3 mmol) of triethylamine, 2 ml (30 mmol) of acrylonitrile and 35 mg (1.5 mmol) of palladium acetate was refluxed under an atmosphere of argon for 16 hr. The mixture was diluted with 100 ml of 1 N hydrochloric acid and the resulting precipitate was collected by filtration. The precipitate was washed with ether and air dried to give an off-white solid, mp 130°-133°.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washThe precipitate was washed with ether and air
  3. customdried
  4. customto give an off-white solid, mp 130°-133°

Sources & evidence

ORD record
ord-06203c6214ca4e7f8aae0a8a0b876f17
Source dataset
uspto-grants-1983_09
Patent number
US04405518

Reaction notes

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