4,4'-Difluorobenzophenone → 2,2-Bis(4-fluorophenyl)oxirane

HRID 1638490Notes

Reaction equation

HRID 1638490 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[F:9][C:10]1[CH:24]=[CH:23][C:13]([C:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[O:15])=[CH:12][CH:11]=1>CS(C)=O>[F:9][C:10]1[CH:24]=[CH:23][C:13]([C:14]2([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[O:15][CH2:4]2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 95824,4'-DifluorobenzophenoneHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)

Product 1

HCID 139839372,2-Bis(4-fluorophenyl)oxiraneYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of dimethyl oxosulphonium methylide was prepared under nitrogen from sodium hydride (0.1 mol) and powdered trimethyl oxosulphonium iodide (0.1 mol) in dry dimethyl sulphoxide (100 ml). A solution of 4,4'-difluorobenzophenone (0.08 mol) in dimethyl sulphoxide (40 ml) was added dropwise at room temperature and the solution heated at 50° for 2 hours. After cooling to room temperature the solution was extracted with diethyl ether (400 ml), washed with water (3×250 ml), and dried over anhydrous sodium sulphate. Removal of the solvent gave 1,1-bis-(4-fluorophenyl)-ethylene oxide (95%) as a colourless oil.

Workup

  1. temperaturethe solution heated at 50° for 2 hours
  2. extractionwas extracted with diethyl ether (400 ml)
  3. washwashed with water (3×250 ml)
  4. dry with materialdried over anhydrous sodium sulphate
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-e15ec24ad6d94923b4f56126608872ac
Source dataset
uspto-grants-1989_11
Patent number
US04880457

Reaction notes

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