Tetrahydrofuran → 1-[4-(1,1,2,2-Tetrafluoro-2-phenylethyl)phenyl]ethan-1-one

HRID 1284280Notes

Reaction equation

HRID 1284280 reaction equation
[F:1][C:2]([C:13]1C=CC(C#N)=[CH:15][CH:14]=1)([F:12])[C:3]([F:11])([F:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[O:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1.[CH3:26][Mg]Br>CCOCC.O>[F:1][C:2]([C:13]1[CH:14]=[CH:15][C:24]([C:25](=[O:21])[CH3:26])=[CH:23][CH:22]=1)([F:12])[C:3]([F:10])([F:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 20372267HCID 20372267, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 203722211-[4-(1,1,2,2-Tetrafluoro-2-phenylethyl)phenyl]ethan-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 3.3 g. (0.0118 mole) of 4-(α,α,β,β-tetrafluorophenethyl)-benzonitrile in 25 ml. of dry, peroxidefree tetrahydrofuran is added dropwise to a stirred solution of about 0.03 mole of methylmagnesium bromide in 25 ml. of absolute ether in a nitrogen atmosphere. The mixture is stirred at reflux for about 26 hours. After cooling in an ice-bath, the adduct is hydrolyzed by the dropwise addition of about 5 ml. of water and the mixture is diluted with about 50 ml. of ether. The organic phase is decanted and the gelatinous precipitate is washed thoroughly with ether. The combined ethereal extracts are washed once with water, extracted with 15 ml. of ice-cold 6N hydrochloric acid in several portions, and then washed with water and dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure leaves the product as the oily solid residue. Sublimation at 95°-100°C. and 0.02 mm. gives purified material as white crystals, m.p. 128°-133°C. A sample for analysis, m.p. 134°-135.5 °C., is obtained by repeated recrystallization from hexane and resublimation.

Workup

  1. customof dry
  2. temperatureat reflux for about 26 hours
  3. temperatureAfter cooling in an ice-bath
  4. additionthe adduct is hydrolyzed by the dropwise addition of about 5 ml
  5. customThe organic phase is decanted
  6. washthe gelatinous precipitate is washed thoroughly with ether
  7. washThe combined ethereal extracts are washed once with water
  8. extractionextracted with 15 ml
  9. washof ice-cold 6N hydrochloric acid in several portions, and then washed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. customEvaporation of the solvent under reduced pressure
  12. customleaves the product as the oily solid residue
  13. customat 95°-100°C.
  14. customgives
  15. custompurified material as white crystals, m.p. 128°-133°C
  16. customA sample for analysis, m.p. 134°-135.5 °C., is obtained
  17. customrecrystallization from hexane and resublimation

Sources & evidence

ORD record
ord-a1cd14e05e864bff91828ca7d0be10fb
Source dataset
uspto-grants-1976_08
Patent number
US03978127

Reaction notes

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