Methanol → Bis(3-bromophenyl)methanone
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=NNC(N)=S)[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[CH:10]=2)[CH:5]=[CH:6][CH:7]=1.C[OH:22].NNC(N)=S>CC(O)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[CH:10]=2)=[O:22])[CH:5]=[CH:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Bis(3-bromophenyl) ketone thiosemicarbazone (14) Into a round bottom flask containing the appropriate ketone (1.044 g, 3.07 mmol), 35 mL of anhydrous methanol were added and the solution was refluxed for about 15 minutes. To the warm ketone solution, thiosemicarbazide (0.294 g, 3.23 mmol) and 1% solution of HOAc (1.5 mL) were added. The reaction mixture was refluxed under nitrogen atmosphere for 46 h, at which point, the solvent was evaporated and, the crude reaction mixture was purified by flash chromatography (20% EtOAc/80% hex) to obtain 0.231 g (0.559 mmol) of the product in an 18% yield.