Water → HCID 22227324, compound

HRID 21998Notes

Reaction equation

HRID 21998 reaction equation
Br[C:2]([F:16])([F:15])[C:3](F)([F:13])[O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1.O>[Zn].C(#N)C>[F:13][C:3]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)=[C:2]([F:16])[F:15]

Participants

5

Reactant 2

HCID 962WaterHCID 18990557HCID 18990557, compound

Product 1

HCID 22227324HCID 22227324, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
79 °C

Procedure

Acetonitrile (300 ml) and granular zinc (30.0 g) are combined in a 1 liter round bottomed flask and stirred at 75° C. under nitrogen as 4-(2-bromotetrafluoroethoxy)benzaldehyde (111.39 g, 0.37 mole) is added slowly by dropping addition funnel. The resulting mixture is stirred and heated at 79° C. for 12 hours. After filtration to remove zinc salts and unreacted zinc, the acetonitrile is removed under vacuum on a rotary evaporator. The resulting oily residue is flash distilled on a rotary evaporator under high vacuum (26.6 Pa) to provide 47.33 g (0.234 mole) of a water white oil in 63.3 percent yield.

Workup

  1. additionis added slowly
  2. additionaddition funnel
  3. filtrationAfter filtration
  4. customto remove zinc salts and unreacted zinc
  5. customthe acetonitrile is removed under vacuum on a rotary evaporator
  6. distillationdistilled on a rotary evaporator under high vacuum (26.6 Pa)

Sources & evidence

ORD record
ord-d32ce7e50ce74a6abd953f8a517f7829
Source dataset
uspto-grants-1995_06
Patent number
US05426164

Reaction notes

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