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

HRID 1462643Notes

Reaction equation

HRID 1462643 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 atomsphere of argon for 16 hr. The mixture was diluted with 100 ml of 1N 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-000257a72c2a4ef8ab31339e999f207e
Source dataset
uspto-grants-1984_07
Patent number
US04460781

Reaction notes

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