Water → N-(4-bromo-2-isopropylphenyl)acetamide
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH:9]([CH3:11])[CH3:10])[CH:3]=1.O.[C:13](OC(=O)C)(=[O:15])[CH3:14]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:13](=[O:15])[CH3:14])=[C:4]([CH:9]([CH3:11])[CH3:10])[CH:3]=1Participants
4
Procedure
A solution of 4-bromo-2-iso-propyl-phenylamine (780 mg, 3.64 mmol) in acetic anhydride (4 mL) was stirred at room temperature over night. The reaction was poured into water and the resulting white precipitate was filtered off and dried under vacuum to give N-(4-bromo-2-iso-propyl-phenyl)-acetamide as a light pink solid (0.770 g, 83%); 1H NMR (300 MHz, DMSO-d6): δ 9.39(s, 1H), 7.43(d, 1H, J=2.4 Hz), 3.16(m, 1H), 2.04(s, 3H), 1.13(d, 6H, J=7 Hz); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=dichloromethane; Rf=0.21