Potassium Carbonate → 9-[4-(9,10-Diphenyl-2-anthryl)phenyl]-9H-carbazole

HRID 1774097Notes

Reaction equation

HRID 1774097 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:22]3C=CC=[CH:24][CH:23]=3)[C:6]3[C:11]([C:12]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.[CH:28]1[C:40]2[N:39]([C:41]3[CH:46]=[CH:45][C:44](B(O)O)=[CH:43][CH:42]=3)[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]=2[CH:31]=[CH:30][CH:29]=1.[C:50]1(C)[CH:55]=CC=C[C:51]=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+].C1(C)C=CC=CC=1.C(O)C>[C:16]1([C:12]2[C:11]3[C:6]([C:5]([C:22]4[CH:23]=[CH:24][CH:55]=[CH:50][CH:51]=4)=[C:4]4[C:13]=2[CH:14]=[C:15]([C:30]2[CH:31]=[CH:32][C:40]([N:39]5[C:38]6[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=6[C:42]6[C:41]5=[CH:46][CH:45]=[CH:44][CH:43]=6)=[CH:28][CH:29]=2)[CH:2]=[CH:3]4)=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 222471632-Bromo-9,10-diphenylanthraceneHCID 231208274-(9H-Carbazol-9-yl)phenylboronic Acid

Product 1

HCID 579231609-[4-(9,10-Diphenyl-2-anthryl)phenyl]-9H-carbazoleYield 54%

Reagents, catalysts & solvents 3

HCID 178476740HCID 178476740, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

In a 100 mL three neck flask were put 2.0 g (4.9 mmol) of 2-bromo-9,10-diphenylanthracene, 1.4 g (4.9 mmol) of 4-(9H-carbazol-9-yl)phenylboronic acid, and 0.15 g (0.50 mmol) of tri(ortho-tolyl)phosphine, and the atmosphere in the flask was replaced with nitrogen. To this mixture were added 15 mL of toluene, 15 mL of ethanol, and 10 mL of an aqueous potassium carbonate solution (2.0 mol/L). This mixture was deaerated while being stirred under reduced pressure. Then, the atmosphere in the flask was replaced with nitrogen. To this mixture was added 23 mg (0.10 mmol) of palladium(1) acetate. This mixture was refluxed at 100° C. for 20 hours. Then, after this mixture was cooled to room temperature, about 50 mL of toluene was added thereto, and the mixture was filtered through a filter paper. The obtained mixture was washed with water, and the aqueous layer was extracted with toluene. The extract solution and the organic layer were combined and washed with a saturated saline solution, and the organic layer was dried with magnesium sulfate. This mixture was gravity filtered. The obtained filtrate was concentrated to give a light yellow solid. This solid was washed with toluene to give the object of the synthesis as 1.5 g of a light yellow powdered solid in a yield of 54%.

Workup

  1. temperatureThen, after this mixture was cooled to room temperature
  2. filtrationthe mixture was filtered through a filter paper
  3. washThe obtained mixture was washed with water
  4. extractionthe aqueous layer was extracted with toluene
  5. washwashed with a saturated saline solution
  6. dry with materialthe organic layer was dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe obtained filtrate was concentrated
  9. customto give a light yellow solid
  10. washThis solid was washed with toluene
  11. customto give

Sources & evidence

ORD record
ord-79f3ef8ac6a54f7bb9fd7d7bb8337bd6
Source dataset
uspto-grants-2016_02
Patent number
US09257654B2

Reaction notes

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