Ethanol → HCID 86727987, compound

HRID 2169688Notes

Reaction equation

HRID 2169688 reaction equation
[Br:1][C:2]1[C:3]2[C:8]([C:9](Br)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.CC1(C)C(C)(C)OB([C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]([C:35]3[S:36][CH:37]=[CH:38][CH:39]=3)=[CH:27][CH:26]=2)O1.C([O-])([O-])=O.[Na+].[Na+].CCO>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>[Br:1][C:2]1[C:3]2[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:9]([C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]([C:35]3[S:36][CH:37]=[CH:38][CH:39]=3)=[CH:27][CH:26]=2)=[C:10]2[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]2

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 682269,10-DibromoanthraceneHCID 86727988HCID 86727988, compound

Product 1

HCID 86727987HCID 86727987, compoundYield 53.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 13.4 g (40 mmol) of 9,10-dibromoanthracene, 20.1 g (60 mmol) of 4,4,5,5-tetramethyl-2-(4-(thiophen-2-yl)naphthalen-1-yl)-1,3,2-dioxaborolane, 0.46 g (0.4 mmol) of tetrakis(triphenylphosphine)palladium, 30 ml of 2M Na2CO3, 80 ml of EtOH and 160 ml toluene was degassed and placed under nitrogen, and then heated at 90° C. for 24 h. After finishing the reaction, the mixture was allowed to cool to room temperature. The organic layer was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica(hexane-dichloromethane) to give product 9.9 g (53%) as a yellow solid.

Workup

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

Sources & evidence

ORD record
ord-3ac6ecf2dd3c410ea5f7adf68c345039
Source dataset
uspto-grants-2015_06
Patent number
US09048437B2

Reaction notes

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