m-Chloroperbenzoic acid → HCID 59568682, compound

HRID 1474204Notes

Reaction equation

HRID 1474204 reaction equation
[Cl: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>[Cl: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 66643858HCID 66643858, compound

Product 1

HCID 59568682HCID 59568682, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-5-ethenyl-2-benzofuran-1(3H)-one (1.1 g, 5.7 mmol) in DCM (40 mL) was added m-CPBA (1.9 g, 8.5 mmol). The solution was allowed to stir at RT for 16 hours. Analysis by TLC and LC showed formation of the desired product, along with some untouched starting material. The reaction was diluted with DCM (200 mL), washed with aqueous Na2S2O3 and Na2CO3, dried over sodium sulfate, concentrated, and purified by silica gel flash chromatography to afford 4-chloro-5-oxiran-2-yl-2-benzofuran-1(3H)-one.

Sources & evidence

ORD record
ord-f0c64ee63a904a5dba5a1509465e6851
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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