Sodium Cyanide → (4-Fluoro-2,6-dimethyl-phenyl)-acetonitrile

HRID 254474Notes

Reaction equation

HRID 254474 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([CH3:11])[C:3]=1[CH2:4]Br.[C-:12]#[N:13].[Na+]>C(O)C.O>[F:10][C:8]1[CH:9]=[C:2]([CH3:1])[C:3]([CH2:4][C:12]#[N:13])=[C:6]([CH3:11])[CH:7]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 226726412-(Bromomethyl)-5-fluoro-1,3-dimethylbenzene

Product 1

HCID 58951703(4-Fluoro-2,6-dimethyl-phenyl)-acetonitrile

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A solution of 1.86 g (9 mmol) 2,6-dimethyl-4-fluoro-benzyl bromide and 0.420 g (9 mmol) sodium cyanide in 21 ml ethanol/water 6:1 was heated to reflux for 4h. The cooled reaction mixture was concentrated and extracted with ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered and evaporated. Filtration of the residue through a silica gel pad with heptane/ethyl acetate 1:1 provided (4-fluoro-2,6-dimethyl-phenyl)-acetonitrile as colourless solid: MS (EI): 163.1 (M+.), 148.1 ((M-CH3)+.), 136.1 ((M-HCN)+., 100%).

Workup

  1. temperatureto reflux for 4h
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated
  4. extractionextracted with ethyl acetate
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. filtrationFiltration of the residue through a silica gel pad with heptane/ethyl acetate 1:1 provided (4-fluoro-2,6-dimethyl-phenyl)-acetonitrile as colourless solid

Sources & evidence

ORD record
ord-5d0223a8eac8424f8f1fabe3869f7d23
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Reaction notes

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