Water → 2-(2-Chlorophenyl)-2-(4-fluorophenyl)oxirane

HRID 1638487Notes

Reaction equation

HRID 1638487 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])=[O:17])=[CH:12][CH:11]=1.O>CS(C)=O>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:16]1([C:13]2[CH:12]=[CH:11][C:10]([F:9])=[CH:15][CH:14]=2)[O:17][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 74547Methanone, (2-chlorophenyl)(4-fluorophenyl)-

Product 1

HCID 135184762-(2-Chlorophenyl)-2-(4-fluorophenyl)oxiraneYield 90%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of dimethyl oxosulphonium methylide was prepared under nitrogen from sodium hydride (0.03 mol) and powdered trimethyl oxosulphonium iodide (0.03 mol) in dry dimethylsulphoxide (DMSO; 30 ml). A solution of o-chlorophenyl p-fluorophenyl ketone (0.025 mol) in DMSO (10 ml) was added dropwise at room temperature. The solution was then heated at 50° for 1.5 hours, cooled to room temperature and poured into water. The solution was extracted with diethyl ether (100 ml), washed with water (3×100 ml), and dried over anhydrous sodium sulphate. Removal of the solvent gave 1-o-chlorophenyl-1-p-fluorophenyl ethylene oxide (90%) as a colourless liquid.

Workup

  1. temperatureThe solution was then heated at 50° for 1.5 hours
  2. extractionThe solution was extracted with diethyl ether (100 ml)
  3. washwashed with water (3×100 ml)
  4. dry with materialdried over anhydrous sodium sulphate
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-5046f025dec742548d61e312e95de839
Source dataset
uspto-grants-1989_11
Patent number
US04880457

Reaction notes

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