Carbazole → 9-(4-Bromobutyl)-9H-carbazole

HRID 1965915Notes

Reaction equation

HRID 1965915 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5]Br.[H-].[Na+].[CH:9]1[C:21]2[NH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1>CN(C=O)C>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][N:20]1[C:21]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[C:14]2[C:19]1=[CH:18][CH:17]=[CH:16][CH:15]=2

Participants

5

Reactant 3

HCID 6854CarbazoleHCID 80561,4-DibromobutaneHCID 24758Sodium hydride

Product 1

HCID 139067719-(4-Bromobutyl)-9H-carbazoleYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,4-Dibromobutane (640.2 g, 30 mol) and sodium hydride (30.1 g, 0.60 mol, 55%) were mixed in 500 mL of DMF under an argon atmosphere. Carbazole (100.0 g, 0.60 mol) was slowly added and the reaction mixture was stirred for 6 hours at room temperature. DMF was removed by vacuum distillation. Then, 9-(4-bromobutyl)-9H-carbazole was purified in a fresh column. The resulting product was purified by silica gel column chromatography (eluent: ethyl acetate:hexane=1:50 v/v) to yield 112 g (62%) of 9-(4-bromobutyl)-9H-carbazole (Compound 8).

Workup

  1. customDMF was removed by vacuum distillation
  2. customThen, 9-(4-bromobutyl)-9H-carbazole was purified in a fresh column
  3. customThe resulting product was purified by silica gel column chromatography (eluent: ethyl acetate:hexane=1:50 v/v)

Sources & evidence

ORD record
ord-0c875bdb84674311a6b36d53203011c5
Source dataset
uspto-grants-2013_04
Patent number
US08420231B2

Reaction notes

Loading…