Ethanol → 2,7-bis(5-methoxybiphenyl-2-yl)-9-phenyl-9H-carbazole

HRID 1753705Notes

Reaction equation

HRID 1753705 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:16]1([N:22]2[C:34]3[CH:33]=[C:32](B4OC(C)(C)C(C)(C)O4)[CH:31]=[CH:30][C:29]=3[C:28]3[C:23]2=[CH:24][C:25](B2OC(C)(C)C(C)(C)O2)=[CH:26][CH:27]=3)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:53]([O-:56])([O-])=O.[Na+].[Na+].[CH3:59][CH2:60]O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:32]2[CH:31]=[CH:30][C:29]3[C:28]4[C:23](=[CH:24][C:25]([C:2]5[CH:7]=[CH:6][C:5]([O:56][CH3:53])=[CH:4][C:3]=5[C:59]5[CH:60]=[CH:12][CH:11]=[CH:10][CH:15]=5)=[CH:26][CH:27]=4)[N:22]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:34]=3[CH:33]=2)=[C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:4]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 675132132-Bromo-5-methoxy-1,1'-biphenylHCID 902975249-Phenyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

Product 1

HCID 903427912,7-bis(5-methoxybiphenyl-2-yl)-9-phenyl-9H-carbazoleYield 67%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 10 g (38.2 mmol) of 2-bromo-5-methoxybiphenyl, 8.6 g (17.4 mmol) of 9-phenyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole, 0.4 g (0.35 mmol) of tetrakis(triphenylphosphine)palladium, 30 ml of 2M Na2CO3, 60 ml of EtOH and 150 ml toluene was degassed and placed under nitrogen, and then heated at 110° C. for 12 h. After finishing the reaction, the mixture was allowed to cool to room temperature. The reaction mixture was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was evaporated in vacuum. The residue was purified by column chromatography on silica(hexane-dichloromethane) afforded a white solid (7.1 g, 11.7 mmol, 67%).

Workup

  1. customwas degassed
  2. customthe reaction
  3. temperatureto cool to room temperature
  4. extractionThe reaction mixture was extracted with ethyl acetate and water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customthe solvent was evaporated in vacuum
  7. customThe residue was purified by column chromatography on silica(hexane-dichloromethane)

Sources & evidence

ORD record
ord-da192fb348db453ba07d52f4efd603be
Source dataset
uspto-grants-2015_10
Patent number
US09166177B2

Reaction notes

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