Pyrimidine → 4-Bromo-2,6-difluoroaniline
Reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH2:4].[Br:10]Br.N1C=CC=NC=1>C(Cl)(Cl)Cl>[Br:10][C:7]1[CH:8]=[C:2]([F:1])[C:3]([NH2:4])=[C:5]([F:9])[CH:6]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In chloroform, commercially available compound [U], 2,6-difluoroaniline, is brominated with bromine in the presence of pyrimidine to yield compound [V], 4-bromo-2,6-difluoroaniline. In NMP, compound [V] is cyanated with copper (I) cyanide to form a copper complex. The copper complex is decomposed with EDA, to yield compound [W], 4-amino-3,5-difluorobenzonitrile. Compound [W] is converted into its corresponding diazonium salt with concentrated sulfuric acid in glacial acetic acid. In hydrobromic acid, the diazonium salt is brominated with copper (I) bromide to yield compound [X], 4-bromo-3,5-difluorobenzonitrile. Compound [X] is reacted with gaseous hydrogen chloride in anhydrous ethanol to yield compound [Y], 4-bromo-3,5-difluorobenzimidate hydrogen chloride. In ethanol, compound [Y] is reacted with gaseous ammonia to yield compound [Z], 4-bromo-3,5-difluorobenzamidine hydrogen chloride.
Sources & evidence
- ORD record
- ord-4c6e38c38bb04a22a52be013b388244b
- Source dataset
- uspto-grants-1993_04
- Patent number
- US05200110
Reaction notes
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