2-Chlorobenzonitrile → 2-(Cyano(4-fluorophenyl)methyl)benzonitrile

HRID 2351577Notes

Reaction equation

HRID 2351577 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]1[CH:16]=[CH:15][C:11]([CH2:12][C:13]#[N:14])=[CH:10][CH:9]=1.Cl[C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[C:20]#[N:21]>CN(C)C=O>[C:20]([C:19]1[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=1[CH:12]([C:13]#[N:14])[C:11]1[CH:15]=[CH:16][C:8]([F:7])=[CH:9][CH:10]=1)#[N:21]

Participants

5

Reactant 3

HCID 133912-ChlorobenzonitrileHCID 68016Benzeneacetonitrile, 4-fluoro-HCID 23665647Potassium tert-butoxide

Product 1

HCID 27739372-(Cyano(4-fluorophenyl)methyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 700 gr potassium tert-butoxide in 3.6 ltr N,N-dimethylformamide (DMF) is added gradually a solution of 401.4 gr 4-fluorobenzylcyanide and 429.2 gr 2-chlorobenzonitrile in 1.2 ltr DMF, maintaining an internal temperature between 25° C. and 30° C. (ice bath). The reaction mixture is subsequently stirred for one hour at ambient temperature and quenched with dilute hydrochloric acid. Extractive work-up with diethylether gives the product 2-cyano-4'-fluorobenzhydrylcyanide.

Workup

  1. temperaturemaintaining an internal temperature between 25° C. and 30° C. (ice bath)
  2. customquenched with dilute hydrochloric acid

Sources & evidence

ORD record
ord-83b353e67a3e47b9b31a2a139c9fa280
Source dataset
uspto-grants-1989_10
Patent number
US04873344

Reaction notes

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