Potassium Carbonate → 5-(3-(3,5-Dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)-2-fluorobenzonitrile

HRID 405700Notes

Reaction equation

HRID 405700 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=O)[C:10]([F:13])([F:12])[F:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:15]([C:18]1[CH:19]=[CH:20][C:21]([F:26])=[C:22]([CH:25]=1)[C:23]#[N:24])(=[O:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:10]([F:13])([F:12])[F:11])=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][C:21]([F:26])=[C:22]([CH:25]=2)[C:23]#[N:24])=[O:17])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27582311-(3,5-Dichlorophenyl)-2,2,2-trifluoroethan-1-oneHCID 224583893'-Cyano-4'-fluoroacetophenone

Product 1

HCID 866421895-(3-(3,5-Dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)-2-fluorobenzonitrileYield 46%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

163 mg of 1-(3,5-Dichloro-phenyl)-2,2,2-trifluoro-ethanone (VIa) (Journal of Physical Organic Chemistry (1989), 2(4), 363-6), 486 mg of 5-acetyl-2-fluoro-benzonitrile (CAS:288309-07-9) and 276 mg of potassium carbonate in 5 ml of dry toluene were refluxed for 72 hours. The solvent was then evaporated under reduced pressure and the residue was purified on silica gel (eluent hexane/ethyl acetate 6:1) affording 5-[3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-but-2-enoyl]-2-fluoro-benzonitrile as a yellow resin in 46% yield (solidified on standing). 1H-NMR (CDCl3, δ in ppm): 8.05-8.11 (m, 2H), 7.33-7.43 (m, 3H), 7.15 (s, 2H).

Workup

  1. customThe solvent was then evaporated under reduced pressure
  2. customthe residue was purified on silica gel (eluent hexane/ethyl acetate 6:1)

Sources & evidence

ORD record
ord-90326a1cc41442708b215db59f93bddc
Source dataset
uspto-grants-2014_06
Patent number
US08754053B2

Reaction notes

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