Potassium Carbonate → 2-(2-Chloro-3-trifluoromethyl-phenoxy)-butyronitrile

HRID 1254970Notes

Reaction equation

HRID 1254970 reaction equation
CS([O:5][CH:6]([CH2:9][CH3:10])[C:7]#[N:8])(=O)=O.[Cl:11][C:12]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:15]=[CH:14][C:13]=1O.C(=O)([O-])[O-].[K+].[K+].C(OC)(C)(C)C>C(#N)C.O>[Cl:11][C:12]1[C:17]([C:18]([F:19])([F:20])[F:21])=[CH:16][CH:15]=[CH:14][C:13]=1[O:5][CH:6]([CH2:9][CH3:10])[C:7]#[N:8]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 15413tert-Butyl methyl etherHCID 27366012-Chloro-3-(trifluoromethyl)phenolHCID 154676912-(Methanesulfonyloxy)-butyronitrile

Product 1

HCID 687350702-(2-Chloro-3-trifluoromethyl-phenoxy)-butyronitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 2-(methanesulfonyloxy)-butyronitrile (204 mg, 1.25 mmol) (prepared following Marco et. al., Tetrahedron, 2000, 56, 2525-31) 2-chloro-3-trifluoromethylphenol (196 mg, 1.0 mmol) and potassium carbonate (172 mg, 1.25 mmol) in acetonitrile (5 ml) was stirred for 1 hour at 95° C. The mixture was shaken between tBuOMe and water and the ethereal phase dried with Na2SO4, filtered over a silicagel pad and evaporated to give as yellowish oil 2-(2-chloro-3-trifluoromethyl-phenoxy)-butyronitrile; 1H-NMR (CDCl3): 1.27 t, 3H, 2.20 m, 2H, 2.40 s, 3H, 4.78 t, 1H, 7.34, d, 1H; 7.39, t, 1H, 7.48 d, 1H.

Workup

  1. dry with materialthe ethereal phase dried with Na2SO4
  2. filtrationfiltered over a silicagel pad
  3. customevaporated

Sources & evidence

ORD record
ord-2a187544f3ea4e37bd4d380196138f44
Source dataset
uspto-grants-2013_06
Patent number
US08455663B2

Reaction notes

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