2-Nitroaniline → 4-Bromo-2-nitroaniline

HRID 617201Notes

Reaction equation

HRID 617201 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[Br:11]C1C(=O)C(Br)=CC(Br)(Br)C=1>C(Cl)Cl>[Br:11][C:9]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=1

Participants

4

Reactant 2

HCID 69462-NitroanilineHCID 884332,4,4,6-Tetrabromocyclohexa-2,5-dienone

Product 1

HCID 701324-Bromo-2-nitroanilineYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-nitroaniline (5 g, 36.2 mmol) in CH2Cl2 (100 ml) was cooled to -10° C., and treated by 90% 2,4,4,6-tetrabromo-2,5-cyclohexadienone (19.8 g, 43.5 mmol) in 5 portions. The mixture was stirred at -10° C.-0° C. for 1 hr. After being warmed to room temperature, the reaction mixture was washed by 2N NaOH (60 ml) and brine (50 ml), dried over Na2SO4 and evaporated. Flash chromatography on silica gel (5% EtOAc/Hexane) gave 7.40 g (94%) of 17 as a yellow solid: mp 109-110 (lit. mp 112-113° C.); 1H NMR δ 8.27 (1H, d, J=2.3), 7.43 (1H, dd, J=8.9, 2.4), 6.73 (1H, d, J=8.8), 6.09 (NH, brs).

Workup

  1. washthe reaction mixture was washed by 2N NaOH (60 ml) and brine (50 ml)
  2. dry with materialdried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-842e0496708549e9b7bf9e94db55bbe0
Source dataset
uspto-grants-1999_09
Patent number
US05948797

Reaction notes

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