4-Cyanophenol → 4-(2,2,2-Trifluoroethoxy)benzonitrile

HRID 843993Notes

Reaction equation

HRID 843993 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].CS(O[CH2:17][C:18]([F:21])([F:20])[F:19])(=O)=O>CN(P(N(C)C)(N(C)C)=O)C.Cl>[F:19][C:18]([F:21])([F:20])[CH2:17][O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 130194-CyanophenolHCID 24758Sodium hydrideHCID 5565652,2,2-Trifluoroethyl Methanesulfonate

Product 1

HCID 109545944-(2,2,2-Trifluoroethoxy)benzonitrileYield 31.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

To a solution 4-cyanophenol (5.0 grams, 42.0 mmole) in HMPT (40 ml) was added sodium hydride (1.68 grams, 42.0 mmole) and stirred for 15 minutes at room temperature. Via syringe 2,2,2-trifluoroethyl methane sulphonate (8.98 grams, 50.4 mmole) was added and the mixture was stirred at 140° C. over night. The mixture was cooled to room temperature, diluted with 300 ml ice water and 50 ml 2 N hydrochloric acid and extracted with diethyl ether. The combined extracts were washed with water, 1N sodium hydroxide and brine, dried over Na2SO4, filtered, and concentrated to an oil which was purified via flash chromatography on silica using 25% diethyl ether/hexane as eluent to give an oil (2.68 g). Synthesis 727 (1980).

Workup

  1. stirringthe mixture was stirred at 140° C. over night
  2. temperatureThe mixture was cooled to room temperature
  3. extractionextracted with diethyl ether
  4. washThe combined extracts were washed with water, 1N sodium hydroxide and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to an oil which
  8. customwas purified via flash chromatography on silica using 25% diethyl ether/hexane as eluent

Sources & evidence

ORD record
ord-eccc8fc2aaf047e2a20feeb3c1351b83
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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