m-Chloroperbenzoic acid → HCID 59568692, compound

HRID 1186942Notes

Reaction equation

HRID 1186942 reaction equation
[Br:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH:12]=[CH2:13].C1C=C(Cl)C=C(C(OO)=[O:22])C=1>C(Cl)Cl>[Br:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH:12]1[CH2:13][O:22]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66643894HCID 66643894, compound

Product 1

HCID 59568692HCID 59568692, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution 4-bromo-5-ethenyl-2-benzofuran-1(3H)-one (2.00 g, 8.37 mmol) in DCM (20 mL) was slowly added mCPBA (2.60 g, 8.37 mmol) at 0° C. The flask was warmed to room temperature and the mixture was then stirred for 12 hours. Analysis by TLC as well as LC indicated that reaction had gone to completion. The reaction mixture was washed with aqueous Na2S2O3, NaHCO3, and water. The organic layer was washed with brine and then concentrated to dryness. The residue was purified over silica gel to give 4-bromo-5-oxiran-2-yl-2-benzofuran-1(3H)-one.

Workup

  1. customat 0° C
  2. customAnalysis by TLC as well as LC indicated that reaction
  3. washThe reaction mixture was washed with aqueous Na2S2O3, NaHCO3, and water
  4. washThe organic layer was washed with brine
  5. concentrationconcentrated to dryness
  6. customThe residue was purified over silica gel

Sources & evidence

ORD record
ord-4c31d5a18b4442b2a5daeae15679b410
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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