N-bromobutanimide → 3'-Bromo-4'-hydroxy-5'-(trifluoromethyl)acetophenone
Reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:5]=1)=[O:3].[Br:15]N1C(=O)CCC1=O>C(#N)C>[Br:15][C:8]1[CH:9]=[C:4]([C:2](=[O:3])[CH3:1])[CH:5]=[C:6]([C:11]([F:12])([F:13])[F:14])[C:7]=1[OH:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
4-Hydroxy-3-(trifluoromethyl)acetophenone (4 g) was initially introduced in acetonitrile (150 ml) and N-bromosuccinimide (4.5 g, dissolved in 100 ml acetonitrile) was added dropwise at −10° C. After addition was complete, the cooling bath was removed and the mixture was stirred for 5 h. After standing overnight, the volume of solvent was reduced to a quarter and the residue was treated with n-heptane/water. After separating off the organic phase, this was washed once with 5% strength sodium thiosulfate solution and once with water. The precipitate formed in the course of this (6.9 g) was filtered off with suction and directly reacted further in the next stage.