Potassium Cyanide → HCID 66890579, compound

HRID 253273Notes

Reaction equation

HRID 253273 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:6]([O:10][CH3:11])=[C:7]([F:9])[CH:8]=1.[C-:20]#[N:21].[K+]>CN(C=O)C>[F:9][C:7]1[CH:8]=[C:3]([CH2:2][C:20]#[N:21])[CH:4]=[C:5]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:6]=1[O:10][CH3:11]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 66891035HCID 66891035, compound

Product 1

HCID 66890579HCID 66890579, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(Chloromethyl)-1-fluoro-2-(methyloxy)-3-[(phenylmethyl)oxy]benzene (2.88 g, 10.26 mmol.) was taken into DMF (15 mL) followed by addition of potassium cyanide (1.0 g, 15.4 mmol.) and the resulting mixture was allowed to stir at room temperature over 12 hours. The mixture was then partitioned with ethyl ether and water and the organic phase washed with water (3×) then saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. Filtration and concentration gave {3-fluoro-4-(methyloxy)-5-[(phenylmethyl)oxy]phenyl}acetonitrile (2.69 g, 97% yield) as a clear oil. GCMS for C16H14O2FN: 271 (M+).

Workup

  1. customThe mixture was then partitioned with ethyl ether and water
  2. washthe organic phase washed with water (3×)
  3. dry with materialsaturated aqueous sodium chloride and dried over anhydrous magnesium sulfate
  4. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-ed2b03070fd348de9402605d1dc22771
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

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