Sodium Cyanide → HCID 22378378, compound

HRID 1956569Notes

Reaction equation

HRID 1956569 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]=1[CH2:15]Br.[C-:17]#[N:18].[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]=1[CH2:15][C:17]#[N:18]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 22378381HCID 22378381, compound

Product 1

HCID 22378378HCID 22378378, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 21.0 g (70.57 mmol) of (2-chloro-6-phenoxy-phenyl)-bromomethane in 16.5 ml of ethanol is added dropwise at 80° C. to a solution of 4.5 g (91.74 mmol) of sodium cyanide in 9.2 ml of water and 2.3 ml of ethanol and the reaction mixture is boiled under reflux for 4 hours. After cooling, the mixture is concentrated using a rotary evaporator, the residue is taken up in ethyl acetate and the organic phase is washed 2× with water and 1× with brine, dried over sodium sulfate, concentrated and chromatographed on silica gel with ethyl acetate to yield 10.82 g (44.40 mmol)=63% of (2-chloro-6-phenoxyphenyl)-acetonitrile in the form of a brown oil; TLC (silica gel; ethyl acetate; UV): Rf =0.42; 1H-NMR (CDCl3, 200 MHz): 3.96 (s, 2H); 6.74-7.46 (m, 8H)

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated
  4. customa rotary evaporator
  5. washthe organic phase is washed 2× with water and 1× with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customchromatographed on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-89fe084e52ef47e2af3336c9230ba3fd
Source dataset
uspto-grants-1998_07
Patent number
US05780500

Reaction notes

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