Acetonitrile → HCID 18956451, compound

HRID 2380006Notes

Reaction equation

HRID 2380006 reaction equation
C(#N)C.BrC(F)COCC(F)Br.[CH3:13][C:14]1[CH:15]=[C:16]([O:21][C:22](F)([F:27])[C:23]([F:26])([F:25])Br)[CH:17]=[CH:18][C:19]=1[CH3:20]>[Zn].O.CCCCCC>[F:27][C:22]([O:21][C:16]1[CH:17]=[CH:18][C:19]([CH3:20])=[C:14]([CH3:13])[CH:15]=1)=[C:23]([F:25])[F:26]

Participants

7

Reactant 3

HCID 6342AcetonitrileHCID 18956471HCID 18956471, compoundHCID 57107014HCID 57107014, compound

Product 1

HCID 18956451HCID 18956451, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
50 °C

Procedure

Acetonitrile (200 mL) and zinc (50 g, 0.765 mol) are transferred to an oven-dried two liter three-necked Morton flask fitted with a mechanical stirrer, reflux condenser, and thermocouple. The mixture is stirred and heated to 50° C. by means of a heating mantle and temperature controller. The mixture is assayed for water (700 ppm) and the temperature is increased to 65° C. The bromofluoroethyl ether, 3,4-dimethyl-l-(2-bromotetrafluoroethoxy)benzene (187.04 g, 0.621 mole) is added over a period of thirty minutes to the stirring mixture. The temperature of the mixture is then increased to 77° C. and the mixture is stirred overnight. Gas chromatographic analysis of the mixture shows no remaining starting material. The mixture is transferred to a 2 L round-bottomed flask using hexane and water to rinse out the reaction vessel. The solvents (water, hexane and acetonitrile) are then removed by rotary evaporation at 65° C. and 100 mm Hg (13.33 kPa). Under these conditions a small amount of the product is carried over with the solvent. The pressure is then reduced to about 2 mm Hg (0.26 kPa) which causes the product, monomer, 3,4-dimethylphenyl perfluorovinyl ether, to distill over as a clear liquid. Yield 108 g (87 percent yield, purity 94 percent).

Workup

  1. customfitted with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperaturethe temperature is increased to 65° C
  4. temperatureThe temperature of the mixture is then increased to 77° C.
  5. stirringthe mixture is stirred overnight
  6. customThe mixture is transferred to a 2 L round-bottomed flask
  7. washto rinse out the reaction vessel
  8. customThe solvents (water, hexane and acetonitrile) are then removed by rotary evaporation at 65° C.
  9. distillationto distill over as a clear liquid

Sources & evidence

ORD record
ord-1ee5cb1b04ef42bcabd3fd341309d660
Source dataset
uspto-grants-1994_11
Patent number
US05364917

Reaction notes

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