N-bromobutanimide → 4-Bromo-3-chloro-2-nitroaniline

HRID 2101996Notes

Reaction equation

HRID 2101996 reaction equation
[Cl:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C1C(=O)N([Br:19])C(=O)C1>C1COCC1>[Br:19][C:8]1[CH:7]=[CH:6][C:4]([NH2:5])=[C:3]([N+:9]([O-:11])=[O:10])[C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1010683-Chloro-2-nitroaniline

Product 1

HCID 265991564-Bromo-3-chloro-2-nitroanilineYield 11.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Chloro-2-nitro aniline (5.0 g, 28.97 mmol) and NBS (5.42 g, 30.42 mmol) were combined in THF (200 mL) and stirred at rt for 15 h. Concentration and purification (SiO2, EtOAc/hexanes) afforded the title compound (0.84 g): 1HNMR (400 MHz, CDCl3) δ 7.46 (d, J=8.9 Hz, 1H), 6.63 (d, J=8.9 Hz, 1H), 4.7 (s, 2H); MS (ESI) m/z 253 (M+1).

Workup

  1. concentrationConcentration and purification (SiO2, EtOAc/hexanes)

Sources & evidence

ORD record
ord-17647e2488444674b3b9a20e08ed17ce
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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