Potassium Cyanide → 4-Bromo-3-(trifluoromethyl)phenylacetonitrile

HRID 592137Notes

Reaction equation

HRID 592137 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[C:9]([C:14]([F:17])([F:16])[F:15])[CH:8]=1)(=O)=O.[C-:18]#[N:19].[K+]>C(O)C.O>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][C:18]#[N:19])=[CH:8][C:9]=1[C:14]([F:17])([F:16])[F:15]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 866579514-Bromo-3-(trifluoromethyl)benzyl methanesulfonate

Product 1

HCID 459337024-Bromo-3-(trifluoromethyl)phenylacetonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-bromo-3-(trifluoromethyl)benzyl methanesulfonate 46-4 (1.295 g, 3.75 mmol) in ethanol (10 mL) was added a solution of potassium cyanide (364 mg, 5.6 mmol) in water (2 mL). The mixture was refluxed for 2 hours. After the mixture was cooled down to the room temperature, all the solvents were evaporated and the residue was redissolved in dichloromethane (50 mL), washed with water and brine, dried over Na2SO4, and concentrated to dryness to give 2-(4-bromo-3-(trifluoromethyl)phenyl)acetonitrile 46-5 as dark brown oil, which was used for next step directly. MS m/z 264.1 (M+1)

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. customwere evaporated
  3. dissolutionthe residue was redissolved in dichloromethane (50 mL)
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-68c6a1513b0243d09de6da5516d00593
Source dataset
uspto-grants-2016_01
Patent number
US09238646B2

Reaction notes

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