Bromine → 2-Bromo-1-(4-iodophenyl)ethanone
Reaction equation
[Br:1]Br.[I:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1>C(O)(=O)C>[Br:1][CH2:11][C:10]([C:7]1[CH:8]=[CH:9][C:4]([I:3])=[CH:5][CH:6]=1)=[O:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of bromine (79.3 g, 508 mmol) in glacial acetic acid (50 mL) was added at room temperature to a solution of 1-(4-Iodo-phenyl)-ethanone (Aldrich, 125 g, 508 mmol) in glacial acetic acid (600 mL). The mixture was stirred for 10 h, then concentrated under reduced pressure and the residue was diluted with ethyl acetate (100 mL), and washed with brine (3×50 mL). The organic layer was concentrated, and the residue was crystallized from ethyl ether to provide the title compound as a yellow solid (150 g, 462 mmol, 91% yield). 1H NMR (300 MHz, CDCl3) δ 4.39 (s, 2H), 7.69 (d, J=8.5 Hz, 2H), 7.87 ppm (d, J=8.5 Hz, 2H); MS (DCl/NH3) m/z 246 (M−Br)+264 (M−Br+NH4)+.