Benzoyl chloride → 2,2,3,3,3-pentafluoro-1-phenylpropan-1-one

HRID 1763072Notes

Reaction equation

HRID 1763072 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:10][C:11](I)([F:16])[C:12]([F:15])([F:14])[F:13].CCCCCC>C(Cl)Cl>[C:2]1([C:1]([C:11]([F:16])([F:10])[C:12]([F:15])([F:14])[F:13])=[O:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8058HexaneHCID 9636Iodopentafluoroethane

Product 1

HCID 2384182,2,3,3,3-pentafluoro-1-phenylpropan-1-oneYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Under protective gas, 35 g (0.25 mol) of benzoyl chloride in 150 ml of CH2Cl2 are initially introduced at about -20° C. into a round-bottomed flask. 67 g (0.27 mol) of pentafluoroethyl iodide are first condensed in and 66.7 g (0.27 mol) of phosphorous acid trisdiethylamide are then metered in. The reaction mixture is subsequently stirred at 0° C. for 5 hours more. After addition of the same volume of hexane to the reaction mixture, 2 phases are formed. After phase separation, the lower phase is carefully extracted using hexane; the combined hexane phases are concentrated and distilled under reduced pressure. 20.8 g (58% yield) of pentafluoroethyl phenyl ketone of b.p. 76-77/40 mbar are obtained.

Workup

  1. customare formed
  2. customAfter phase separation
  3. extractionthe lower phase is carefully extracted
  4. concentrationthe combined hexane phases are concentrated
  5. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-a4d236dd281d44e48161701b595265b0
Source dataset
uspto-grants-1989_05
Patent number
US04835318

Reaction notes

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