4-Bromobenzophenone → 2-(4-Bromophenyl)-2-phenyloxirane

HRID 509191Notes

Reaction equation

HRID 509191 reaction equation
[I-].[CH3:2][S+](C)C.[H-].[Na+].[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:16])=[CH:11][CH:10]=1>C1COCC1>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:2][O:16]2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 70304-BromobenzophenoneHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodide

Product 1

HCID 157379652-(4-Bromophenyl)-2-phenyloxirane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
55 °C

Procedure

To a stirring solution of trimethylsulfonium iodide (5.27 g, 19.15 mmol) in THF (20 mL) was added sodium hydride (0.957 g, 23.94 mmol) and the reaction mixture was stirred at 55° C. for 6 h. A solution of (4-bromophenyl)(phenyl)methanone 50 (5.0 g, 19.15 mmol) in THF (10 mL) was added and the mixture was stirred an additional 16 h at 55° C. The reaction mixture was quenched with water, diluted with ether and layer separated. The organic layer was dried over Na2SO4, filtered and concentrated to afford 2-(4-bromophenyl)-2-phenyloxirane 51 (quantitative yield) as a brown oil.

Workup

  1. stirringthe mixture was stirred an additional 16 h at 55° C
  2. customThe reaction mixture was quenched with water
  3. additiondiluted with ether and layer
  4. customseparated
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-efcbff611ca84aedbee412d5477d7659
Source dataset
uspto-grants-2015_08
Patent number
US09096565B2

Reaction notes

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