Bromine → 2-Bromo-6-nitro-4-phenoxy-phenylamine

HRID 2089561Notes

Reaction equation

HRID 2089561 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:5]=1[NH2:17])([O-:3])=[O:2].[Br:18]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[Br:18][C:6]1[CH:7]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]=1[NH2:17]

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 51737522-Nitro-4-phenoxyaniline

Product 1

HCID 684774322-Bromo-6-nitro-4-phenoxy-phenylamineYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-Nitro-4-phenoxy-phenylamine (2.3 g, 10 mmol) prepared in Preparation 1 was dissolved in DCM (30 mL), Br2 (720 ul, 35%) was added thereto at 0° C., and the mixture was stirred for 2 h. After completion of the reaction, saturated aqueous sodium thiosulfate solution was added. The resulting mixture was extracted with EtOAc, and dried over MgSO4. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (2.84 g, Yield 92%).

Workup

  1. additionwas added
  2. extractionThe resulting mixture was extracted with EtOAc
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c28651cfecab4742a78afb884d28c9a0
Source dataset
uspto-grants-2013_05
Patent number
US08436038B2

Reaction notes

Loading…