Hydrogen Bromide → 5-Bromo-2-chloronitrobenzene

HRID 2278391Notes

Reaction equation

HRID 2278391 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](N)=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].N([O-])=O.[Na+].[BrH:16]>O>[Br:16][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 124774-Chloro-3-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 8179745-Bromo-2-chloronitrobenzeneYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 4-chloro-3-nitro-phenylamine (17.2 g, 0.1 mol) in 260 mL HBr (48%) at 0° C. was added dropwise NaNO2 (13.8 g, 0.2 mol) in water. The reaction mixture was stirred for 1 h at 0° C. then CuBr (24 g, 0.17 mol) was added in portions to the mixture and stirred for an additional 1 h. Water was added, the mixture allowed to warm to room temperature and was then extracted with EtOAc. The crude product was purified by silica gel column chromatography to give the title compound (13 g, 55%).

Workup

  1. stirringstirred for an additional 1 h
  2. temperatureto warm to room temperature
  3. extractionwas then extracted with EtOAc
  4. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b88e2bb166a44465857f82d701531ce2
Source dataset
uspto-grants-2015_09
Patent number
US09133180B2

Reaction notes

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