Bromine → 2-Bromo-3,4-difluoro-6-nitroaniline

HRID 414377Notes

Reaction equation

HRID 414377 reaction equation
[F:1][C:2]1[C:8]([F:9])=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[Br:13]Br>C(O)(=O)C>[Br:13][C:7]1[C:8]([F:9])=[C:2]([F:1])[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]=1[NH2:6]

Participants

4

Reactant 2

HCID 24408BromineHCID 1571514,5-Difluoro-2-nitroaniline

Product 1

HCID 140717912-Bromo-3,4-difluoro-6-nitroanilineYield 87.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Into a solution of 4,5-difluoro-2-nitroaniline (3.7 g) in acetic acid (27 ml) was added bromine (6.8 g) dropwise at 50° to 56° C. and stirred for 2.5 hours. The reaction mixture was poured into ice water (60 ml) and the resulting precipitate was collected by filtration and washed with water sufficiently to give the title compound (4.7 g) as yellow prisms, mp 105° C.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashed with water sufficiently

Sources & evidence

ORD record
ord-515cd08e8c1e4cd2b4283bee16487ca6
Source dataset
uspto-grants-1988_12
Patent number
US04791225

Reaction notes

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