Acetic Anhydride → 9-Acetyl-3-bromocarbazole

HRID 403149Notes

Reaction equation

HRID 403149 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[C:15](OC(=O)C)(=[O:17])[CH3:16]>OS(O)(=O)=O.C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:15](=[O:17])[CH3:16])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 2524463-Bromocarbazole

Product 1

HCID 17148799-Acetyl-3-bromocarbazoleYield 52.1%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 6212ChloroformSolvent

Procedure

A solution of 3-bromo-9H-carbazole (10.00 g, 40.6 mmol), acetic anhydride (8.30 g, 81 mmol) together with 2 drops of H2SO4 in chloroform (150 mL) was refluxed overnight. After cooling to room temperature, the solution was washed with water. Upon evaporation of the solvent, the crude product was purified by crystallization from hexane/DCM and hexane/EtOAc to yield 1-(3-bromo-9H-carbazol-9-yl)ethanone (6.1 g, 51% yield) as a light yellow solid.

Workup

  1. washthe solution was washed with water
  2. customUpon evaporation of the solvent
  3. customthe crude product was purified by crystallization from hexane/DCM and hexane/EtOAc

Sources & evidence

ORD record
ord-448e779b27c0471baaa8051f1674588c
Source dataset
uspto-grants-2014_06
Patent number
US08748012B2

Reaction notes

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