N-bromobutanimide → 3-Bromo-9-(p-tolyl)-9H-carbazole

HRID 516492Notes

Reaction equation

HRID 516492 reaction equation
[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([N:7]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)=[CH:3][CH:2]=1.[Br:21]N1C(=O)CCC1=O>ClCCl>[Br:21][C:11]1[CH:10]=[CH:9][C:8]2[N:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:20])=[CH:6][CH:5]=3)[C:19]3[C:14]([C:13]=2[CH:12]=1)=[CH:15][CH:16]=[CH:17][CH:18]=3

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 157986519-(p-Tolyl)carbazole

Product 1

HCID 714639373-Bromo-9-(p-tolyl)-9H-carbazoleYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 9-p-tolyl-9H-carbazole (0.82 g, 3.2 mmol) in dichloromethane (DCM)(30 mL) was added N-bromosuccinimide (NBS) at about 0° C. The whole was stirred at about 0° C. to about room temperature (RT) overnight. The resulting solution was purified by flash column (silica gel, hexanes to hexanes/dichloromethane 8:1). After removal of solvent, a white solid (Compound 13) was obtained (1.0 gram, in 93% yield).

Workup

  1. customThe resulting solution was purified by flash column (silica gel, hexanes to hexanes/dichloromethane 8:1)
  2. customAfter removal of solvent

Sources & evidence

ORD record
ord-01669ec1732a48838ef351a2ec242fb1
Source dataset
uspto-grants-2015_08
Patent number
US09112159B2

Reaction notes

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