3,5-Difluoro-4-(2-phenyldiazenyl)phenol → 4-Amino-3,5-difluorophenol
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:17])[CH:5]=[C:6]([F:16])[C:7]=1[N:8]=NC1C=CC=CC=1>CO.[Pd]>[NH2:8][C:7]1[C:2]([F:1])=[CH:3][C:4]([OH:17])=[CH:5][C:6]=1[F:16]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
20.4 g (0.09 mol) of 3,5-difluoro-4-(phenyldiazenyl)phenol from Example 1 and 0.5 g of Pd/C (10%) were initially charged in 120 ml of methanol. The solution was degassed and aerated with hydrogen. The mixture was stirred at room temperature under a 1 bar hydrogen atmosphere for 16 hours. On completion of hydrogen uptake, the catalyst was filtered off and the filtrate concentrated on a rotary evaporator. The residue was chromatographed on silica gel (n-hexane/ethyl acetate, 3:1). The resulting solid was stirred with n-hexane and dried. 7.6 g (60%) of 4-amino-3,5-difluorophenol were obtained as a yellow-brown solid.