Hexane → 9-(4'-(9H-carbazol-9-yl)biphenyl-4-yl)-3-(4-vinylphenyl)-9H-carbazole

HRID 1481946Notes

Reaction equation

HRID 1481946 reaction equation
[CH:1]1[C:13]2[N:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][C:23]([N:26]5[C:38]6[CH:37]=[CH:36][C:35](Br)=[CH:34][C:33]=6[C:32]6[C:27]5=[CH:28][CH:29]=[CH:30][CH:31]=6)=[CH:22][CH:21]=4)=[CH:16][CH:15]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:40](P(C(C)(C)C)C(C)(C)C)(C)(C)[CH3:41].[CH3:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58]>C1(C)C=CC=CC=1>[CH:1]1[C:13]2[N:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][C:23]([N:26]5[C:38]6[CH:37]=[CH:36][C:35]([C:55]7[CH:54]=[CH:53][C:58]([CH:40]=[CH2:41])=[CH:57][CH:56]=7)=[CH:34][C:33]=6[C:32]6[C:27]5=[CH:28][CH:29]=[CH:30][CH:31]=6)=[CH:22][CH:21]=4)=[CH:16][CH:15]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 86682764HCID 86682764, compound

Product 1

HCID 866827639-(4'-(9H-carbazol-9-yl)biphenyl-4-yl)-3-(4-vinylphenyl)-9H-carbazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
85 °C

Procedure

9-(4′-(9H-carbazol-9-yl)biphenyl-4-yl)-3-bromo-9H-carbazole (0.5 g, 0.88 mmol) and 4-vinyl boronic acid (0.14 g, 0.98 mmol) and Pd(dba)3 (0.097 g, 0.01 mmol), CsCO3 (0.289 g, 0.88 mmol) were dissolved in toluene (25 mL). Tri-t-butyl phosphine 10 wt % in hexane (0.053 g, 0.026 mmol) was added and the reaction mixture was stirred vigorously while refluxed at 85° C. for 24 h. The reaction mixture was cooled down to room temperature, diluted with toluene and filtered through a celite filter bed. The organic extract was evaporated to dryness and purified by silica column chromatography using dichloromethane and pet-ether (40-60° C.) to give slightly brownish colour powder as the product (0.3 g)

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. filtrationfiltered through a celite filter bed
  3. extractionThe organic extract
  4. customwas evaporated to dryness
  5. custompurified by silica column chromatography
  6. customdichloromethane and pet-ether (40-60° C.)

Sources & evidence

ORD record
ord-2c288a9391454e40b67833631954b9a2
Source dataset
uspto-grants-2016_08
Patent number
US09410080B2

Reaction notes

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