Potassium Carbonate → 2,2'-(5-(8-bromodibenzo[b,d]furan-2-yl)-1,3-phenylene)bis(1-phenyl-1H-benzo[d]imidazole)

HRID 1486378Notes

Reaction equation

HRID 1486378 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([C:30]3[N:34]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:33]4[CH:41]=[CH:42][CH:43]=[CH:44][C:32]=4[N:31]=3)[CH:12]=[C:13]([C:15]3[N:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:18]4[CH:26]=[CH:27][CH:28]=[CH:29][C:17]=4[N:16]=3)[CH:14]=2)O1.Br[C:47]1[CH:60]=[CH:59][C:50]2[O:51][C:52]3[CH:57]=[CH:56][C:55]([Br:58])=[CH:54][C:53]=3[C:49]=2[CH:48]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[Br:58][C:55]1[CH:56]=[CH:57][C:52]2[O:51][C:50]3[CH:59]=[CH:60][C:47]([C:9]4[CH:14]=[C:13]([C:15]5[N:19]([C:20]6[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=6)[C:18]6[CH:26]=[CH:27][CH:28]=[CH:29][C:17]=6[N:16]=5)[CH:12]=[C:11]([C:30]5[N:34]([C:35]6[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=6)[C:33]6[CH:41]=[CH:42][CH:43]=[CH:44][C:32]=6[N:31]=5)[CH:10]=4)=[CH:48][C:49]=3[C:53]=2[CH:54]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 822902,8-DibromodibenzofuranHCID 901995352,2'-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene)bis(1-phenyl-1H-benzo[d]imidazole)

Product 1

HCID 1176072502,2'-(5-(8-bromodibenzo[b,d]furan-2-yl)-1,3-phenylene)bis(1-phenyl-1H-benzo[d]imidazole)Yield 56%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,2′-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene)bis(1-phenyl-1H-benzo[d]imidazole) (3.00 g, 5.10 mmol), 2,8-dibromodibenzo[b,d]furan (1.83 g, 5.61 mmol), tetrakis(triphenylphosphine) palladium(0) (0.30 g, 0.26 mmol), potassium carbonate (2.11 g, 15.30 mmol), 1,4-dioxane (90.00 mL), and water (18.00 mL) was degassed with bubbling argon for 50 min. The reaction mixture was then heated to 80° C. and was stirred overnight (16.5 hours), maintaining an argon atmosphere. Consumption of the starting material was confirmed by thin-layer chromatography and the reaction was cooled to room temperature. The product was extracted with dichloromethane, dried, and purified by silica gel column chromatography with ethyl acetate in dichloromethane as the eluent. The product fractions were then dried and the product was collected to yield Compound 14 (2.00 g, 56%). Confirmed by LCMS (APCI): calculated for C44H27BrN4O (M+H): 707. Found: 707.

Workup

  1. customwas degassed with bubbling argon for 50 min
  2. temperaturemaintaining an argon atmosphere
  3. customConsumption of the starting material
  4. temperaturethe reaction was cooled to room temperature
  5. extractionThe product was extracted with dichloromethane
  6. customdried
  7. custompurified by silica gel column chromatography with ethyl acetate in dichloromethane as the eluent
  8. customThe product fractions were then dried
  9. customthe product was collected

Sources & evidence

ORD record
ord-9f980e24c3f246619cfe71346ddc67d2
Source dataset
uspto-grants-2016_08
Patent number
US09425408B2

Reaction notes

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