tert-butyl 4-((E)-2-(3,4-dimethylphenyl)vinyl)-2-(4-fluoroanilino)benzoate → 4-((E)-2-(3,4-dimethylphenyl)vinyl)-2-(4-fluoroanilino)benzoic acid

HRID 2191791Notes

Reaction equation

HRID 2191791 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]2[CH:23]=[CH:22][C:14]([C:15]([O:17]C(C)(C)C)=[O:16])=[C:13]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH:12]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]>FC(F)(F)C(O)=O>[CH3:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]2[CH:23]=[CH:22][C:14]([C:15]([OH:17])=[O:16])=[C:13]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH:12]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

3

Reactant 1

HCID 68962926tert-butyl 4-((E)-2-(3,4-dimethylphenyl)vinyl)-2-(4-fluoroanilino)benzoate

Product 1

HCID 576680744-((E)-2-(3,4-dimethylphenyl)vinyl)-2-(4-fluoroanilino)benzoic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Trifluoroacetic acid 10 mL solution of tert-butyl 4-((E)-2-(3,4-dimethylphenyl)vinyl)-2-(4-fluoroanilino)benzoate was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, and the obtained residue was refined by reversed-phase silica gel column chromatography [eluent; 85-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to give 4-((E)-2-(3,4-dimethylphenyl)vinyl)-2-(4-fluoroanilino)benzoic acid.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f11b0930ad1740d6b37b5421ff05be5b
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

Loading…