Sodium Cyanide → 3-Fluoro-4-methoxyphenylacetonitrile

HRID 2050096Notes

Reaction equation

HRID 2050096 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[C:5]([F:11])[CH:4]=1.[CH2:12]([N:18](CCCCCC)CCCCCC)CCCCC.[C-]#N.[Na+]>O>[F:11][C:5]1[CH:4]=[C:3]([CH2:2][C:12]#[N:18])[CH:8]=[CH:7][C:6]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 66022TrihexylamineHCID 27745534-(Bromomethyl)-2-fluoro-1-methoxybenzene

Product 1

HCID 1362513-Fluoro-4-methoxyphenylacetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(bromomethyl)-2-fluoroanisole (45.8 g, 0.21 mol), trihexylamine (1.4 g) and sodium cyanide (20.5 g, 0.42 mol) in water (50 ml) is heated at 60°-65° C. for 18 hours. The mixture is cooled and extracted in its ether, washed with water, saturated sodium chloride solution and dried (CNa2SO4). Evaporation of the solvent gives a solid, (33.2 g): m.p. 42°-46° C.

Workup

  1. temperatureis heated at 60°-65° C. for 18 hours
  2. temperatureThe mixture is cooled
  3. extractionextracted in its ether
  4. washwashed with water, saturated sodium chloride solution
  5. dry with materialdried (CNa2SO4)
  6. customEvaporation of the solvent
  7. customgives a solid, (33.2 g)

Sources & evidence

ORD record
ord-0b5c1373a8294b4196cf6dbc99e9e2f5
Source dataset
uspto-grants-1980_04
Patent number
US04199595

Reaction notes

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