Sodium Cyanide → HCID 58174138, compound

HRID 1255891Notes

Reaction equation

HRID 1255891 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[N:7][CH:8]=1.[C-:20]#[N:21].[Na+]>CCO>[F:17][C:16]([F:19])([F:18])[C:13]1[CH:14]=[CH:15][C:10]([O:9][C:6]2[N:7]=[CH:8][C:3]([CH2:2][C:20]#[N:21])=[CH:4][CH:5]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 58174152HCID 58174152, compound

Product 1

HCID 58174138HCID 58174138, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of 5-chloromethyl-2-(4-trifluoromethylphenoxy)-pyridine (1.8 g, 6.27 mmol) in EtOH (12 mL) was added NaCN (1.23 g, 25 mmol). The reaction mixture was heated to 50° C. for 16 h. More ethanol (6 mL) was added, and the reaction mixture clarified. After an additional 3 h, the solvent was removed in vacuo, the residue taken up in Et2O and washed with H2O. The organic layer was dried with Na2SO4, suction filtered and concentrated in vacuo. The residue was purified by flash chromatography (50% Et2O in petroleum ether over SiO2) to yield [6-(4-trifluoromethylphenoxy)-pyridin-3-yl]-acetonitrile (1.3 g) as a pink solid; 1H NMR (300 MHz, CDCl3) δ 8.17-8.09 (m, 1H), 7.81-7.71 (m, 1H), 7.70-7.61 (m, 2H), 7.29-7.19 (m, 2H), 7.04 (d, J=8.4 Hz, 1H), 3.73 (s, 2H); EIMS m/z 278 ([M]+).

Workup

  1. customthe solvent was removed in vacuo
  2. washwashed with H2O
  3. dry with materialThe organic layer was dried with Na2SO4, suction
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (50% Et2O in petroleum ether over SiO2)

Sources & evidence

ORD record
ord-a8d6d0076df0443ab74c5b2c0542013a
Source dataset
uspto-grants-2013_06
Patent number
US08461164B2

Reaction notes

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