2-Nitroaniline → 4-Bromo-2-nitroaniline

HRID 964052Notes

Reaction equation

HRID 964052 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-d1a2981dc40f437ba1bb822341e292b7
Source dataset
uspto-grants-1998_06
Patent number
US05767142

Reaction notes

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