Water → 4-Bromo-5-chloro-2-nitroaniline

HRID 1848227Notes

Reaction equation

HRID 1848227 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].C1C(=O)N([Br:19])C(=O)C1.O>CC(O)=O>[Br:19][C:3]1[C:2]([Cl:1])=[CH:8][C:6]([NH2:7])=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 218469994-Bromo-5-chloro-2-nitroanilineYield 96.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 5-chloro-2-nitroaniline (6.0 g, 34.88 mmol) and NBS (6.06 g, 34.0 mmol) in HOAc (240 mL) was stirred at 130° C. for 1 h. The reaction mixture was poured into water. The precipitate was collected by filtration and washed with petroleum ether to give 4-bromo-5-chloro-2-nitroaniline as a light brown solid (8.25 g, 96.5%). 1H NMR (300 MHz, DMSO-d6) δ 8.24 (s, 1H), 7.62 (br s, 2H), 7.29 (s, 1H). LCMS (ESI) m/z 251 (M+H)+.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with petroleum ether

Sources & evidence

ORD record
ord-f7da9f0778cd4107b7c56dec5cb925b8
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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