Trifluoroacetic acid → (E)-3-[1-(3-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid

HRID 1445509Notes

Reaction equation

HRID 1445509 reaction equation
C([O:5][C:6](=[O:24])/[CH:7]=[CH:8]/[C:9]1[CH:13]=[CH:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[CH:18]=2)(=[O:16])=[O:15])[CH:10]=1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[Br:23][C:19]1[CH:18]=[C:17]([S:14]([N:11]2[CH:12]=[CH:13][C:9](/[CH:8]=[CH:7]/[C:6]([OH:24])=[O:5])=[CH:10]2)(=[O:15])=[O:16])[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66646069(E)-3-[1-(3-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester

Product 1

HCID 68526317(E)-3-[1-(3-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acidYield 44.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.0 g (E)-3-[1-(3-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester with 60 ml dichloromethane and 6.0 ml TFA is stirred at ambient temperature for 24 h. The dichloromethane and TFA is evaporated and the residue is coevaporated with toluene for a few times. By this method 0.77 g brown solid is obtained.

Workup

  1. customThe dichloromethane and TFA is evaporated

Sources & evidence

ORD record
ord-e8ad8c61cb5f4c8fa6b4bcec0bf5e1bb
Source dataset
uspto-grants-2010_02
Patent number
US07666868B2

Reaction notes

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