Sodium Sulfite → Ethyl(6-((2,4-dichlorobenzyl)oxy)-1,1-dioxido-1-benzothiophen-3-yl)acetate

HRID 591473Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])=[CH:14][C:9]=2S[CH:7]=1)[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.[O-:37][S:38]([O-:40])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[C:10]2[CH:9]=[CH:14][C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])=[CH:12][C:11]=2[S:38](=[O:40])(=[O:37])[CH:7]=1)[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

To a mixture of ethyl(6-((2,4-dichlorobenzyl)oxy)-1-benzothiophen-3-yl)acetate (10.0 g) in anhydrous DCM (400 mL) was added mCPBA (85%, 15.7 g), and the resulting solution was stirred at 25° C. for 3 d. To the reaction mixture was added Na2SO3 (30.0 g), and the mixture was stirred at 25° C. for 0.5 h. The reaction mixture was washed successively with saturated aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated in vacuo. The residue was washed with EtOAc to give the title compound (8.50 g).

Workup

stirringthe mixture was stirred at 25° C. for 0.5 h
washThe reaction mixture was washed successively with saturated aqueous NaHCO3 and brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
washThe residue was washed with EtOAc

Sources & evidence

ORD record: ord-054e05d73d354d4b90f96785e676bf3d
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238639B2

Reaction notes

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