1-Phenyl-1,2-propanedione → 3-Bromo-1-phenylpropane-1,2-dione
Reaction equation
[C:1]1([C:7](=[O:11])[C:8](=[O:10])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:12]Br>C(Cl)(Cl)Cl>[Br:12][CH2:9][C:8](=[O:10])[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
5.32 kg of 1-phenylpropane-1,2-dione (98.6% by G.C. equivalent to 5.24 kg, 35.4 mole) were dissolved in 36 liters of chloroform and the solution was heated to 50° C. A solution of 5.66 kg (35.4 mole) of bromine in 8 liters of chloroform was added slowly to maintain a gentle reflux and immediate decolorization of the bromine (approximately 6 hours). The solution was cooled to room temperature overnight and was washed with 20 liters of saturated sodium bicarbonate solution and 20 liters of water and dried over sodium sulfate. The solvent was removed under vacuum to obtain 8.2 kg (100% yield) of a green/yellow oil which was used directly for subsequent reactions after estimation of its purity (approximately 75% by G.C. or N.M.R.).