Trimethylsulfonium iodide → 2,2-Bis(3-bromophenyl)oxirane

HRID 1429269Notes

Reaction equation

HRID 1429269 reaction equation
[CH3:1]C([O-])(C)C.[K+].[Br:7][C:8]1[CH:9]=[C:10]([C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Br:22])[CH:17]=2)=[O:15])[CH:11]=[CH:12][CH:13]=1.[I-].C[S+](C)C>CS(C)=O.C(OCC)(=O)C>[Br:7][C:8]1[CH:9]=[C:10]([C:14]2([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Br:22])[CH:17]=3)[CH2:1][O:15]2)[CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 75127Trimethylsulfonium iodideHCID 12731928Bis(3-bromophenyl)methanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 580319912,2-Bis(3-bromophenyl)oxirane

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
30 °C

Procedure

KOt-Bu (2.72 g, 24.26 mmol) was added to a stirred suspension of bis(3-bromophenyl)methanone (7.5 g, 22.06 mmol) and trimethylsulfonium iodide (4.50 g, 22.06 mmol) in DMSO (20 mL) and the resulting mixture was stirred at 30° C. for 8 h. The mixture was diluted with ethyl acetate (500 mL), washed with water (500 mL×3) and brine (500 mL). The organic layer was separated and evaporated in vacuo to afford the title compound which was used directly without further purification.

Workup

  1. washwashed with water (500 mL×3) and brine (500 mL)
  2. customThe organic layer was separated
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-66921278e40d4a5d8e2defeaa44e5cfb
Source dataset
uspto-grants-2015_01
Patent number
US08937150B2

Reaction notes

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