Sodium Hydroxide → 2-(6-Bromo-1-fluorocarbazol-9-yl)phenylamine

HRID 1485587Notes

Reaction equation

HRID 1485587 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-])=O)[C:10]1[C:9]([F:24])=[CH:8][CH:7]=[CH:6][C:5]2=1.[OH-].[Na+]>CCO.[Cl-].[Cl-].[Zn+2]>[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21])[C:10]1[C:9]([F:24])=[CH:8][CH:7]=[CH:6][C:5]2=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 673253476-Bromo-1-fluoro-9-(2-nitrophenyl)-9H-carbazole

Product 1

HCID 673251662-(6-Bromo-1-fluorocarbazol-9-yl)phenylamine

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 702EthanolSolvent

Procedure

67 g (219 mmol) of 6-bromo-1-fluoro-9-(2-nitrophenyl)-9H-carbazole are dissolved in 820 ml of EtOH, 143 g (755 mmol) of ZnCl2 are added at room temperature, and the mixture is heated under reflux for 6 h. The mixture is allowed to come to room temperature over the course of 1 h, 20% NaOH is added, and the phases are separated. The solvent is then removed, and the residue is purified by chromatography. The yield is 44 g (125 mmol), corresponding to 72% of theory.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 6 h
  3. additionis added
  4. customthe phases are separated
  5. customThe solvent is then removed
  6. customthe residue is purified by chromatography

Sources & evidence

ORD record
ord-c411b6bcc3664f3081209f3e5710a715
Source dataset
uspto-grants-2016_08
Patent number
US09422287B2

Reaction notes

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