Water → 3-Bromocarbazole

HRID 2045738Notes

Reaction equation

HRID 2045738 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:14]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:14][C:3]1[CH:2]=[CH:1][C:13]2[NH:12][C:11]3[C:6]([C:5]=2[CH:4]=1)=[CH:7][CH:8]=[CH:9][CH:10]=3

Participants

5

Reactant 3

HCID 962WaterHCID 6854CarbazoleHCID 67184N-bromobutanimide

Product 1

HCID 2524463-BromocarbazoleYield 84.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

16 g of carbazole was dissolved in 80 ml of N,N′-dimethylformamide. To this was added 18 g of N-bromosuccinimide and allowed the reaction to stir at room temperature overnight. The reaction mixture was poured into water and the precipitated white solid was filtered, washed with methanol and dried under vacuum to obtain 20 g of 3-bromocarbazole. It was further 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.

Workup

  1. customthe reaction
  2. filtrationthe precipitated white solid was filtered
  3. washwashed with methanol
  4. customdried under vacuum

Sources & evidence

ORD record
ord-7cbd715b6d364dbcb444e81141e0ae62
Source dataset
uspto-grants-2013_11
Patent number
US08592055B2

Reaction notes

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