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

HRID 2408459Notes

Reaction equation

HRID 2408459 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 TEA 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 TEA is evaporated

Sources & evidence

ORD record
ord-7ddfbcf5b3444cb3b539a34525f18d4d
Source dataset
uspto-grants-2014_08
Patent number
US08815855B2

Reaction notes

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