Bromine → 4-Bromo-2,6-difluoroaniline

HRID 1086393Notes

Reaction equation

HRID 1086393 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>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]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 796472,6-Difluoroaniline

Product 1

HCID 6101914-Bromo-2,6-difluoroaniline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In the method of preparation, Compound [A], 2,6-difluoroaniline, is reacted with bromine in chloroform to yield compound [B], 4-bromo-2,6-difluoroaniline. Compound [B] is mixed with copper (I) cyanide in N-methylpyrrolidone to yield compound [C], 4-cyano-2,6-difluoroaniline. Compound [C] is mixed with sodium nitrite and sulfuric acid in acetic acid to yield a diazonium salt. The diazonium salt is mixed with copper (I) bromide in hydrobromic acid to yield compound [D], 5-cyano-1,3-difluorobenzene.

Sources & evidence

ORD record
ord-4c3f4dee27304111b2cb519bce3daa46
Source dataset
uspto-grants-1991_07
Patent number
US05030382

Reaction notes

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