N-bromobutanimide → 4-Bromo-2,6-difluoroaniline

HRID 2351584Notes

Reaction equation

HRID 2351584 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH2:4].[Br:10]N1C(=O)CCC1=O>CN(C)C=O>[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 67184N-bromobutanimideHCID 796472,6-Difluoroaniline

Product 1

HCID 6101914-Bromo-2,6-difluoroanilineYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Fifty grams (0.39 mole) of 2,6-difluoroaniline was treated with 71.0 g (0.39 mole) of N-bromosuccinimide in 250 ml of dimethylformamide by the procedure of Mitchell, Lai and Williams, J. Org. Chem., 44, 4733 (1979) to give a total yield of 50.2 g (62%) of 4-bromo-2,6-difluoroaniline, m.p.: 64°-66° C.

Sources & evidence

ORD record
ord-80b6a799dfdf482ca36df2ca23b7b04b
Source dataset
uspto-grants-1989_10
Patent number
US04873357

Reaction notes

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