N-bromobutanimide → 3-BroMo-9-dibenzothiophen-4-yl-9H-carbazole

HRID 2172412Notes

Reaction equation

HRID 2172412 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH:9]1[C:17]2[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[S:14][C:13]=2[C:12]([N:22]2[C:34]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:28]3[C:23]2=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:11][CH:10]=1>CN(C=O)C.C(Cl)Cl>[Br:1][C:31]1[CH:32]=[CH:33][C:34]2[N:22]([C:12]3[C:13]4[S:14][C:15]5[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=5[C:17]=4[CH:9]=[CH:10][CH:11]=3)[C:23]3[C:28]([C:29]=2[CH:30]=1)=[CH:27][CH:26]=[CH:25][CH:24]=3

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 58084636HCID 58084636, compound

Product 1

HCID 584795943-BroMo-9-dibenzothiophen-4-yl-9H-carbazoleYield 61.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

N-bromosuccinimide (0.31 g, 1.74 mmol) in 5 mL DMF was added slowly to 9-(dibenzo[b,d]thiophen-4-yl)-9H-carbazole (0.6 g, 1.72 mmol) in 50 mL of DCM at 0° C. The reaction was allowed to warm to room temp and stirred overnight. The reaction mixture was extracted with DCM and dried over MgSO4 and the solvent was evaporated. The residue was purified by column chromatography using DCM:hexane (1:4, v/v) as the eluent to obtain 0.45 g of product.

Workup

  1. extractionThe reaction mixture was extracted with DCM
  2. dry with materialdried over MgSO4
  3. customthe solvent was evaporated
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-acccd9d124b141158c4adbbe7103f1e1
Source dataset
uspto-grants-2015_06
Patent number
US09054323B2

Reaction notes

Loading…