Potassium Cyanide → [4'-(Trifluoromethyl)[1,1'-biphenyl]-4-yl] acetonitrile

HRID 1669285Notes

Reaction equation

HRID 1669285 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[C-:19]#[N:20].[K+].C(OCC)(=O)C.CCCCCC>CN(C)C=O.C(OCC)(=O)C.O>[F:16][C:15]([F:18])([F:17])[C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][C:19]#[N:20])=[CH:4][CH:5]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 3

HCID 9032Potassium CyanideHCID 21226206Ethyl acetate hexaneHCID 222801654-(Bromomethyl)-4'-(trifluoromethyl)-1,1'-biphenyl

Product 1

HCID 20099836[4'-(Trifluoromethyl)[1,1'-biphenyl]-4-yl] acetonitrileYield 45%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4′-bromomethyl-4-trifluoromethyl-biphenyl (0.797 g, 2.53 mmol) and potassium cyanide (0.181 g, 2.78 mmol) in N,N-dimethyl-formamide (6 mL) is stirred for eighty-eight hours at room temperature. The mixture is diluted with ethyl acetate and water. Organic phase is washed with water twice then brine, dried over sodium sulfate, filtered and concentrated. Column chromatography on silica gel with 0-40% ethyl acetate/hexane gradient gives 0.295 g (1.13 mmol, 45%) of title compound.

Workup

  1. washOrganic phase is washed with water twice
  2. dry with materialbrine, dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-24f9df06f3b64fad91b1a6d2b9c4879d
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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