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

HRID 991474Notes

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

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

custompartitioned with ether and water
customThe organic layer was separated
washwashed with brine
dry with materialdried (Na2SO4)
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-c10f84f6b7e74e6a9b7b74e77e82ee41
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06465459B2

Reaction notes

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