Sodium Cyanide → 2-(2,6-Bis(trifluoromethyl)phenyl)acetonitrile

HRID 254477Notes

Reaction equation

HRID 254477 reaction equation
Br[CH2:2][C:3]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:6]=[CH:5][C:4]=1[C:13]([F:16])([F:15])[F:14].[C-:17]#[N:18].[Na+]>CCO.O>[F:14][C:13]([F:16])([F:15])[C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([C:9]([F:12])([F:11])[F:10])[C:3]=1[CH2:2][C:17]#[N:18]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 118513632,6-Bis(trifluoromethyl)benzyl bromide

Product 1

HCID 589518382-(2,6-Bis(trifluoromethyl)phenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A solution of 0.73 g (2.4 mmol) 2-bromomethyl-1,3-bis-trifluoromethyl-benzene and 0.183 g (3.7 mmol) sodium cyanide in 10 ml EtOH/H2O 6:1 (v/v) was hated to reflux for 3h. Then the reaction mixture was evaporated, the residue taken up in water and extracted with tert-butyl methyl ether. The combined extracts were washed with saturated aqueous NaHCO3 solution and brine, dried over Na2SO4 and evaporated. Purification by flash chromatography on silica gel with a gradient of 95:5 to 70:30% heptane/ethyl acetate provided (2,6-bis-trifluoromethyl-phenyl)-acetonitrile as colourless crystalline product of m.p. 84.5-86° C.: MS (EI): 253.0 (M.+ ), 234.1 ((M-F) .+), 233.1 ((M-HF)+.), 184.0 (((M-CF3)+.), 100%).

Workup

  1. temperatureto reflux for 3h
  2. customThen the reaction mixture was evaporated
  3. extractionextracted with tert-butyl methyl ether
  4. washThe combined extracts were washed with saturated aqueous NaHCO3 solution and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customPurification by flash chromatography on silica gel with a gradient of 95:5 to 70

Sources & evidence

ORD record
ord-de33135fe59443bcb0ff58fff42f61a4
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Reaction notes

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