1,4-dimethyl-2,5-diphenylbenzene

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. was degassed to cool to room temperature The organic layer was extracted with ethyl acetate and water dried with anhydrous magnesium sulfate the solvent was removed the residue was purified by column chromatography on silica (hexane-dichloromethane)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2′,5′-Dimethyl-1,1′:4′,1″-terphenyl (180.9 g) was dissolved in pyridine (4296 mL), water (405 mL) was added and the reaction mixture heated to 90° C. Potassium permanganate (KMnO4) (516 g, Sigma-Aldrich) was carefully added and refluxing continued. Additional KMnO4 (235 g) and water (677 mL) were added every 30 minutes for 2 hours. Once addition was complete, refluxing was continued for 18 hours. The reaction mixture was filtered hot through a celite pad, washing the filter cake with boiling water (3×2000 mL). The filtrates were concentrated to remove most of the pyridine before adjusting to pH-1 with concentrated hydrochloric acid. The solids were collected by vacuum filtration, washed with water (2×1400 mL) and dried to give a cream solid. The solid was then refluxed in ethyl acetate (840 mL), cooled, collected by vacuum filtration and washed with ethyl acetate (2×233 mL) to give the product as a cream solid. Yield; 183.8 g. refluxing Once addition refluxing The reaction mixture was filtered hot through a celite pad washing the filter cake with boiling water (3×2000 mL) The filtrates were concentrated to remove most of the pyridine The solids were collected by vacuum filtration washed with water (2×1400 mL) dried to give a cream solid cooled collected by vacuum filtration washed with ethyl acetate (2×233 mL)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. was degassed to cool to room temperature The organic layer was extracted with ethyl acetate and water dried with anhydrous magnesium sulfate the solvent was removed the residue was purified by column chromatography on silica (hexane-dichloromethane)