m-Chloroperbenzoic acid → HCID 59568682, compound

HRID 1848521Notes

Reaction equation

HRID 1848521 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 mCPBA (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. 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 title compound. 1H-NMR (500 MHz, CDCl3) δ ppm 7.86 (d, J=8.0 Hz, 1H), 7.48 (d, J=8.0 Hz, 1H), 5.34 (s, 2H), 4.33 (m, 1H), 3.33 (m, 1H), 2.75 (m, 1H).

Sources & evidence

ORD record
ord-3eef74a01f5c448bac1078ffd08c62b3
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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