Hydrogen Bromide → 4'-Bromo-2'-phenylacetanilide
Reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=2[NH:9][C:10](=[O:12])[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BrH:17]>C(O)(=O)C.C(Cl)(Cl)(Cl)Cl>[C:1]1([C:7]2[CH:16]=[C:15]([Br:17])[CH:14]=[CH:13][C:8]=2[NH:9][C:10](=[O:12])[CH3:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
2-Phenyl-N-acetylaniline (6.21 g, 29.40 mmol) was dissolved in acetic acid (70 mL). Thereto was dropwise added under ice bath a separately prepared solution of hydrogen bromide (6.14 g, 38.42 mmol) dissolved in carbon tetrachloride (19.21 mL) and the mixture was stirred at room temperature overnight. The solution was concentrated under reduced pressure, to the residue was added water (20 mL) and subsequently ethanol (30 mL), and the mixture was stirred under ice bath for 1 hour. The precipitate was collected by filtration, washed with ethanol/water (=1:1), dried under reduced pressure to obtain 2-phenyl-4-bromo-N-acetylaniline (7.79 g).