Ethanol → 2,7-bis(5-methoxybiphenyl-2-yl)-9,9-dimethyl-9H-fluorene

HRID 1753701Notes

Reaction equation

HRID 1753701 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](Br)=[CH:9][CH:10]=3)[C:5]([CH3:17])([CH3:16])[C:4]=2[CH:3]=1.[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23](B(O)O)=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:25]=1.[C:35]([O-:38])([O-])=O.[Na+].[Na+].[CH3:41][CH2:42]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>[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([C:2]2[CH:14]=[CH:13][C:12]3[C:11]4[C:6](=[CH:7][C:8]([C:2]5[CH:14]=[CH:13][C:12]([O:38][CH3:35])=[CH:4][C:3]=5[C:41]5[CH:42]=[CH:7][CH:6]=[CH:5][CH:16]=5)=[CH:9][CH:10]=4)[C:5]([CH3:17])([CH3:16])[C:4]=3[CH:3]=2)=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:25]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 121238762,7-Dibromo-9,9-dimethylfluoreneHCID 85664000(4-Methoxy-2-phenylphenyl)boronic acid

Product 1

HCID 867300012,7-bis(5-methoxybiphenyl-2-yl)-9,9-dimethyl-9H-fluoreneYield 67%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3.52 g (10 mmol) of 2,7-dibromo-9,9-dimethyl-9H-fluorene, 5.5 g (24 mmol) of 5-methoxybiphenyl-2-ylboronic acid, 0.12 g (0.1 mmol) of tetrakis(triphenylphosphine)palladium, 15 ml of 2M Na2CO3, 20 ml of EtOH and 60 ml toluene was degassed and placed under nitrogen, and then heated at 110° C. for 8 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 (3.7 g, 6.7 mmol, 67%); 1H NMR (CDCl3, 400 MHz): chemical shift (ppm) 7.57 (d, J=8.00 Hz, 2H), 7.45 (d, J=9.20 Hz, 2H), 7.21˜7.14 (m, 12H), 7.00˜6.98 (m, 4H), 6.88 (s, 2H), 3.89 (s, 6H), 0.89 (s, 6H).

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-a6fe55e51823493db529d86b94f5fb20
Source dataset
uspto-grants-2015_10
Patent number
US09166177B2

Reaction notes

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