Sulfuric Acid → 9-Acetyl-3-bromocarbazole

HRID 530762Notes

Reaction equation

HRID 530762 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].S(=O)(=O)(O)O>>[C:15]([N:6]1[C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)(=[O:17])[CH3:16]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 2524463-Bromocarbazole

Product 1

HCID 17148799-Acetyl-3-bromocarbazole

Procedure

20 g of 3-bromocarbazole was converted to its acetyl derivative by refluxing with acetic anhydride (3 vol) with traces of conc. sulfuric acid. Aqueous workup yielded an off-white solid, which was then washed with n-hexane and dried under vacuum to obtain 23 g 9-acetyl-3-bromocarbazole, quantitatively. And N-acetyl derivative of carbazole, benzocarbaole and dibenzocarbazoles were prepared following the same procedure.

Workup

  1. customAqueous workup yielded an off-white solid, which
  2. washwas then washed with n-hexane
  3. customdried under vacuum

Sources & evidence

ORD record
ord-47ec478568da421fbd7d36378cc19fdc
Source dataset
uspto-grants-2016_05
Patent number
US09353085B2

Reaction notes

Loading…