Cesium carbonate → 3-[(3,5,6-Trifluoro-4-methylpyridin-2-yl)oxy]benzonitrile

HRID 1636393Notes

Reaction equation

HRID 1636393 reaction equation
F[C:2]1[C:7]([F:8])=[C:6]([CH3:9])[C:5]([F:10])=[C:4]([F:11])[N:3]=1.[C:12]([C:14]1[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=1)#[N:13].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[F:8][C:7]1[C:2]([O:20][C:16]2[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=2)[C:12]#[N:13])=[N:3][C:4]([F:11])=[C:5]([F:10])[C:6]=1[CH3:9]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 133943-CyanophenolHCID 46613162,3,5,6-Tetrafluoro-4-methylpyridine

Product 1

HCID 154533403-[(3,5,6-Trifluoro-4-methylpyridin-2-yl)oxy]benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
45 °C

Procedure

To 2,3,5,6-tetrafluoro-4-methylpyridine (0.71 g, 4.3 mmol) dissolved in acetonitrile (5 mL) was added 3-cyanophenol (0.5 g, 4.2 mmol) and cesium carbonate (1.44 g, 4.4 mmol). The reaction was heated in an oil bath at 45° C. for 16 hours and partitioned with ether and water. The organic layer was separated, washed with brine, dried (Na2SO4), and the solvent removed in vacuo. Chromatography on silica gel with methylene chloride/hexane (7/3) gave 3-[(3,5,6-trifluoro-4-methylpyridin-2-yl)oxy]benzonitrile; NMR (CDCl3) 7.55 (m,2), 7.45 (m,2), 2.24 (s,3) ppm.

Workup

  1. custompartitioned with ether and water
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-8a0802f3cd24486eaa5359fd6aff6c12
Source dataset
uspto-grants-2000_03
Patent number
US06034103

Reaction notes

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