Trifluoroacetic acid → (E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]acrylic acid

HRID 1445508Notes

Reaction equation

HRID 1445508 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][C:20]([Br:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:10]=1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[Br:23][C:20]1[CH:19]=[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:16])=[O:15])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66646304(E)-3-[1-(4-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester

Product 1

HCID 68524810(E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]acrylic acidYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 7.0 g (E)-3-[1-(4-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester with 200 ml dichloromethane and 21.0 ml TFA is stirred at ambient temperature for 24 h. The dichloromethane and TFA is evaporated and the residue is coevaporated with toluene for 3 times. By this method 6.0 g of the title compound is obtained.

Workup

  1. customThe dichloromethane and TFA is evaporated

Sources & evidence

ORD record
ord-c5c20d6075e1456aaf2c3e89d220434d
Source dataset
uspto-grants-2010_02
Patent number
US07666868B2

Reaction notes

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