1-Bromo-3-chloro-2,4-difluoro-5-nitrobenzene → 5-Bromo-3-chloro-2,4-difluoroaniline

HRID 1165409Notes

Reaction equation

HRID 1165409 reaction equation
[F:1][C:2]1[C:7]([Cl:8])=[C:6]([F:9])[C:5]([Br:10])=[CH:4][C:3]=1[N+:11]([O-])=O>O1CCCC1.[Re]>[F:1][C:2]1[C:7]([Cl:8])=[C:6]([F:9])[C:5]([Br:10])=[CH:4][C:3]=1[NH2:11]

Participants

4

Reactant 1

HCID 198616351-Bromo-3-chloro-2,4-difluoro-5-nitrobenzene

Product 1

HCID 198616345-Bromo-3-chloro-2,4-difluoroaniline

Reagents, catalysts & solvents 2

HCID 23947RheniumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

7.6 g of 2,4-difluoro-3-chloro-5-bromonitrobenzene are dissolved in 80 ml of tetrahydrofuran and hydrogenated at from +20° to 25° C. over a period of 4 hours in the presence of 1.7 g of 5% rhenium-on-carbon (hydrogen absorbed: 1.88 l). The reaction mixture is filtered, the solvent is removed by distillation, and the residue is suspended in hexane and filtered off with suction. The title compound of formula ##STR12## is obtained in the form of colourless crystals; m.p. 86°-88° C.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe solvent is removed by distillation
  3. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-a24bcc5dcf1a4a518db0ebb7c5298105
Source dataset
uspto-grants-1990_03
Patent number
US04910018

Reaction notes

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