4-Bromoanisole → HCID 14669906, compound

Participants

Reaction Conditions

Reaction Steps

3-Chloro-6-(4'-propylphenyl)-pyridazine prepared according to a method disclosed in a known literature (m.p.: 127.6°-129.6° C.) (60.0 g) was dissolved in tetrahydrofuran (THF) (700 ml), followed by adding NiCl2 (dppp) (2.5 g) as a catalyst, agitating the mixture at -10° C. for 15 minutes, dropwise adding therto a Grignard reagent obtained by reacting p-bromoanisole (96.5 g) with magnesium in THF, agitating the mixture in an ice bath for one hour, removing the ice bath, agitating it at room temperature for 3 hours, allowing it to stand overnight, adding toluene (500 ml), further adding 6N-hydrochloric acid, separating the resulting organic layer, washing it with water, then with an alkali and further with water till the washing water became neutral, drying with MgSO4, distilling off toluene, purifying the residue according to column chromatography using activated alumina (300 g) and toluene as an eluent, concentrating, and recrystallizing from ethyl acetate (700 ml) to obtain 3-(4'-methoxyphenyl)-6-(4'-propylphenyl)-pyridazine (70 g). This product had a m.p. of 155.9° C., exhibited nematic phase and formed an isotropic liquid at 254° C.

Provenance & Evidence