Chlorosulfonic acid → Methyl 2-[5-bromo-2-(chlorosulfonyl)phenyl]acetate

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.[Cl:13][S:14](O)(=[O:16])=[O:15]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:14]([Cl:13])(=[O:16])=[O:15])=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:3]=1

Participants

Reactant 2

HCID 24638Chlorosulfonic acid

HCID 11746402Methyl 2-(3-bromophenyl)acetate

Product 1

HCID 90150774Methyl 2-[5-bromo-2-(chlorosulfonyl)phenyl]acetate

Procedure

Methyl 2-(3-bromophenyl)acetate (22 g, 67 mmol) was slowly added into ClSO3H at −10° C. After 1 h, the mixture was warmed up to rt and stirred overnight, diluted slowly with ice water and extracted with EA. The organic layer was washed with water, dried over Na2SO4 and evaporated to give compound P15a (17 g, 54%).

Workup

extractionextracted with EA
washThe organic layer was washed with water
dry with materialdried over Na2SO4
customevaporated
customto give compound P15a (17 g, 54%)

Sources & evidence

ORD record: ord-6bdd0a8009b1423cbe5b959f58aecfca
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946446B2

Reaction notes

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