Carbazole → 9-(3-Bromophenyl)-9H-carbazole

HRID 2282793Notes

Reaction equation

HRID 2282793 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][C:15]1[CH:20]=[CH:19][CH:18]=[C:17](I)[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1>ClC1C=CC=CC=1Cl.[Cu]>[Br:14][C:15]1[CH:16]=[C:17]([N:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 6854CarbazoleHCID 11430Potassium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 26541Dibenzo-18-crown-6

Product 1

HCID 586908889-(3-Bromophenyl)-9H-carbazole

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
100 °C

Procedure

4 g of carbazole, 8.08 g of 1-bromo-3-iodobenzene, 13.2 g of potassium carbonate, 3.08 g of copper powder and 0.63 g of dibenzo-18-crown-6 were dissolved in 30 mL of o-dichlorobenzene, and the resulting solution was refluxed at a steady 100° C. After completion of the reaction, the reaction mixture was extracted with dichloromethane and distilled water, and the solvent was dried. The resulting solid was filtered and purified, yielding 9-(3-bromophenyl)-9H-carbazole as an intermediate.

Workup

  1. customAfter completion of the reaction
  2. extractionthe reaction mixture was extracted with dichloromethane
  3. distillationdistilled water
  4. customthe solvent was dried
  5. filtrationThe resulting solid was filtered
  6. custompurified

Sources & evidence

ORD record
ord-c4b9449157cb4858a4b998a402480ab2
Source dataset
uspto-grants-2015_09
Patent number
US09142784B2

Reaction notes

Loading…