4-Chloro-2-nitroaniline → 2-Bromo-4-chloro-6-nitrobenzenamine

HRID 1024039Notes

Reaction equation

HRID 1024039 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[Br:12]N1C(=O)CCC1=O>C(#N)C.C(OCC)(=O)C>[Br:12][C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]=1[NH2:8]

Participants

5

Reactant 2

HCID 69794-Chloro-2-nitroanilineHCID 67184N-bromobutanimide

Product 1

HCID 110648842-Bromo-4-chloro-6-nitrobenzenamineYield 107.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-chloro-2-nitrobenzenamine (5.1 g, 30 mmol) and N-bromosuccinimide (6.2 g, 36 mmol) in acetonitrile (50 mL) was heated at reflux for overnight. It was cooled to room temperature and diluted with ethyl acetate (50 mL). The mixture was washed with saturated aqueous K2CO3 solution (100 mL×2). The organic phase was separated, dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure to afford 109a as a yellow solid (8.1 g, 100%). LCMS: [M+H]+ 253. 1H NMR (500 MHz, CDCl3) δ 8.17 (d, J=2.5 Hz, 1H), 7.71 (d, J=2.5 Hz, 1H), 6.64 (s, 2H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for overnight
  3. washThe mixture was washed with saturated aqueous K2CO3 solution (100 mL×2)
  4. customThe organic phase was separated
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f67c02d0e5064655ad21e3f08bffb6a0
Source dataset
uspto-grants-2014_05
Patent number
US08722676B2

Reaction notes

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