Ethanol → 1,4-dimethyl-2,5-diphenylbenzene

HRID 879909Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5](Br)=[CH:4][C:3]=1[CH3:10].[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+].[CH3:26][CH2:27]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>[C:11]1([C:2]2[CH:7]=[C:6]([CH3:8])[C:5]([C:27]3[CH:26]=[CH:4][CH:3]=[CH:2][CH:7]=3)=[CH:4][C:3]=2[CH3:10])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 52.8 g (200 mmol) of 1,4-dibromo-2,5-Dimethyl benzene, 53.6 g (440 mmol) of phenylboronic acid, 2.3 g (2 mmol) of tetrakis(triphenylphosphine)palladium, 400 ml of 2M Na2CO3, 400 ml of EtOH and 800 ml toluene was degassed and placed under nitrogen, and then heated at 90° C. for 6 hours. After the reaction finish, 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 43.4 g (168 mmol, 84%) as a white solid.

Workup

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

Sources & evidence

ORD record: ord-5faa449727be45adbff9a27c607d9ec5
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993130B2

Reaction notes

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