Pentafluoroaniline → 2,4-Di-tert-butyl-6-[(pentafluoroanilino)methylidene]cyclohexa-2,4-dien-1-one
Reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([CH:15]=NC2C(Br)=CC=CC=2Br)[C:6]=1[OH:25])([CH3:4])([CH3:3])[CH3:2].[F:26][C:27]1[C:33]([F:34])=[C:32]([F:35])[C:31]([F:36])=[C:30]([F:37])[C:28]=1[NH2:29].C(C1C(O)=C(C=C(C(C)(C)C)C=1)C=O)(C)(C)C>>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([CH:15]=[N:29][C:28]2[C:27]([F:26])=[C:33]([F:34])[C:32]([F:35])=[C:31]([F:36])[C:30]=2[F:37])[C:6]=1[OH:25])([CH3:4])([CH3:3])[CH3:2]Participants
4
Procedure
Employing an analogous procedure to that described above for the synthesis of 2,4-bis(tert-butyl)-6-[[(2,6-dibromophenyl)imino]methyl]phenol, 2,3,4,5,6-pentafluoroaniline (0.54 g, 2.9 mmol) was added to 3,5-di-tert-butyl-2-hydroxybenzaldehyde (0.70 g, 2.9 mmol). The product was purified by recrystallisation from hot MeOH and isolated as yellow crystals.