Ethanol → 3,7-Bis(5-methoxybiphenyl-2-yl)dibenzo[b,d]thiophene

HRID 1753708Notes

Reaction equation

HRID 1753708 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][C:12](Br)=[CH:13][C:8]=3[S:7][C:6]=2[CH:15]=1.[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21](B(O)O)=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:23]=1.[C:33]([O-:36])([O-])=O.[Na+].[Na+].[CH3:39][CH2:40]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>[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([C:2]2[CH:3]=[CH:4][C:5]3[C:9]4[CH:10]=[CH:11][C:12]([C:2]5[CH:3]=[CH:4][C:5]([O:36][CH3:33])=[CH:6][C:15]=5[C:39]5[CH:40]=[CH:10][CH:9]=[CH:8][CH:13]=5)=[CH:13][C:8]=4[S:7][C:6]=3[CH:15]=2)=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:23]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 8037593,7-Dibromodibenzo(b,d)thiopheneHCID 85664000(4-Methoxy-2-phenylphenyl)boronic acid

Product 1

HCID 867300063,7-Bis(5-methoxybiphenyl-2-yl)dibenzo[b,d]thiopheneYield 81%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3.42 g (10 mmol) of 3,7-dibromodibenzo[b,d]thiophene, 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, 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) to afford a white solid (4.4 g, 8.1 mmol, 81%).

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-6ee38b1af7ef4ae69d88d9cf2818fa87
Source dataset
uspto-grants-2015_10
Patent number
US09166177B2

Reaction notes

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