N-bromobutanimide → HCID 86696085, compound

HRID 2172414Notes

Reaction equation

HRID 2172414 reaction equation
[CH:1]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[N:19]1[C:31]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2.[Br:32]N1C(=O)CCC1=O>CN(C=O)C>[Br:32][C:28]1[CH:29]=[CH:30][C:31]2[N:19]([C:2]3[CH:3]=[CH:4][C:5]4[C:6]5[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=5)[C:12]5[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=5)[C:18]=4[CH:1]=3)[C:20]3[C:25]([C:26]=2[CH:27]=1)=[CH:24][CH:23]=[CH:22][CH:21]=3

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 595617139-(triphenylen-2-yl)-9H-carbazole

Product 1

HCID 86696085HCID 86696085, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 9-(triphenylen-2-yl)-9H-carbazole (4.7 g, 11.9 mmol) in DMF (24 mL) at 0° C. under N2, NBS (N-bromosuccinimide) (2.1 g, 11.9 mmol) in DMF (24 mL) was added dropwise. After the completion of addition, the reaction mixture was warmed to room temperature overnight with vigorous stirring. The reaction mixture was precipitated with water and the solid was filtered. The pale grey solid was re-dissolved in a small amount of THF, added on a silica plug and flushed with 30% DCM/hexane. The filtrate was dried under vacuum and the white solid was used without further purification (5.5 g, 98 N.

Workup

  1. additionAfter the completion of addition
  2. customThe reaction mixture was precipitated with water
  3. filtrationthe solid was filtered
  4. dissolutionThe pale grey solid was re-dissolved in a small amount of THF
  5. additionadded on a silica plug
  6. customflushed with 30% DCM/hexane
  7. customThe filtrate was dried under vacuum
  8. customthe white solid was used without further purification (5.5 g, 98 N

Sources & evidence

ORD record
ord-a0cd1da2be764b868cc3851b6199da10
Source dataset
uspto-grants-2015_06
Patent number
US09054323B2

Reaction notes

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