Pentane → 2-{4-[5-(4-Tert-butylphenyl)pyridin-2-yl]phenyl}-4,6-di-m-tolyl-1,3,5-triazine

Participants

Reaction Conditions

Reaction Steps

Under a stream of argon, 5.3 ml of a pentane solution containing 7.8 mmol of tert-butyl lithium was slowly added to 25 ml of tetrahydrofuran cooled to −78° C., and 15 ml of tetrahydrofuran in which 1.13 g of 2-bromo-5-(4-tert-butylphenyl)pyridine had been dissolved was further added dropwise to this solution. After stirring at −78° C. for 30 minutes, 2.47 g of dichloro(tetramethylethylenediamine)zinc(II) was added thereto and stirred at −78° C. for 10 minutes and then at room temperature for 2 hours. A 50 ml portion of tetrahydrofuran prepared by dissolving 1.25 g of 2-(4-bromophenyl)-4,6-di-m-tolyl-1,3,5-triazine synthesized by the method of Reference Example 2 and 0.17 g of tetrakis(triphenylphosphine)palladium(0) therein was added to this solution and stirred under heating reflux for 3 hours. The reaction solution was concentrated under a reduced pressure and the thus obtained solid was recrystallized from dichloromethane-methanol. The thus obtained crude product was purified by a silica gel column chromatography (eluting solution hexane:dichloromethane=3:2 to 4:3) and then again recrystallized from dichloromethane-methanol to obtain a white solid of the intended 2-{4-[5-(4-tert-butylphenyl)pyridin-2-yl]phenyl}-4,6-di-m-tolyl-1,3,5-triazine (1.55 g, yield 94%). Its melting point is shown in Table 4. In this case, a distinct point of glass transition was not observed.

Provenance & Evidence