1,2,4-Trimethylbenzene → HCID 86701359, compound

Participants

Reaction Steps

9-bromoanthracene (75.0 g), (4-ethoxynaphthalen-1-yl)boronic acid (78.0 g), Pd(dba)2 (5.0 g), tricyclohexyl phosphine (4.9 g), potassium phosphate (124.0 g), and a mixture solvent (440 ml) of pseudo cumene and t-butyl alcohol (pseudo cumene/t-butyl alcohol=10/1 (volume ratio)) were added to a flask and refluxed for 8 hours. The reaction solution was cooled to room temperature and the precipitated solid were collected by suction filtration. The obtained solid was washed with aqueous solution of EDTA.4Na, water, and methanol in order. It was then dissolved in heated chlorobenzene and then subjected to suction filtration by using a Kiriyama funnel layered with silica gel. The crude product obtained by removing filtrate by distillation under reduced pressure was washed with heptane while being heated to give 9-(4-ethoxynaphthalen-1-yl)anthracene (87.1 g) as a fourteenth intermediate compound. The scheme is shown in the following “Reaction 25”.

Provenance & Evidence