Sodium Cyanide → HCID 12614407, compound

HRID 2049891Notes

Reaction equation

HRID 2049891 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[CH2:9]Cl)=[CH:4][CH:3]=1.[C-:17]#[N:18].[Na+]>CS(C)=O>[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[CH2:9][C:17]#[N:18])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 203438271-(Chloromethyl)-2-(4-fluorophenoxy)benzene

Product 1

HCID 12614407HCID 12614407, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

12.0 g of 2-(4-fluorophenoxy)benzyl chloride are added portionwise over a 30 minute span to a mixture of 2.9 g of sodium cyanide in 120 ml of dimethylsulfoxide. After total addition, the reaction mixture is stirred for 26 hours before being poured onto 150-200 ml of crushed ice. The mixture is extracted four times with 70 ml portions of ether and the combined ether extracts are successively washed four times with 50 ml portions of water, washed once with 25 ml of saturated sodium chloride solution and dried, providing a clear oil. The oil is distilled at 128.5° C. and 0.1 mm to provide 2-(4-fluorophenoxy)benzyl cyanide.

Workup

  1. additionAfter total addition
  2. extractionThe mixture is extracted four times with 70 ml portions of ether
  3. washthe combined ether extracts are successively washed four times with 50 ml portions of water
  4. washwashed once with 25 ml of saturated sodium chloride solution
  5. customdried
  6. customproviding a clear oil
  7. distillationThe oil is distilled at 128.5° C.

Sources & evidence

ORD record
ord-71c0af7c27e64c0e9f29d86bf2c76a6b
Source dataset
uspto-grants-1980_04
Patent number
US04198417

Reaction notes

Loading…