Hydrogen Bromide → 1-(4-Carboxyphenyl)-2-cyanoindole
Reaction equation
C([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[C:15]2[C:23]#[N:24])=[CH:10][CH:9]=1)=[O:7])(C)(C)C.Br>C(O)(=O)C>[C:6]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[C:15]2[C:23]#[N:24])=[CH:10][CH:9]=1)([OH:7])=[O:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3.6 g (0.011 mol) of 1-[4-(tert-butoxycarbonyl)phenyl]-2-cyanoindole was dissolved in 40 ml of acetic acid and 10 ml of 30% hydrogen bromide in acetic acid was added dropwise. After stirring for 10 minutes, the slurry was poured onto 200 g of ice-water, and the resulting precipitate was filtered, washed with water and air-dried, to give 2.8 g (0.0107 mol) of 1-(4-carboxyphenyl)-2-cyanoindole, m.p., 128°-131° C.