Sodium Carbonate → 6-tert-Butyl-4-(3,5-di-tert-butylphenyl)-5-methoxy-2-methylindan-1-one

Participants

Reaction Steps

A mixture of 30.7 g (98.6 mmol) of 4-bromo-6-tertbutyl-5-methoxy-2-methylindanone, 30.6 g (128 mmol) 3,5-di-tert-butylphenylboronic acid, 29.7 g (280 mmol) of Na2CO3, 1.35 g (5.92 mmol; 6 mol. %) of Pd(OAc)2, 3.15 g (11.8 mmol; 12 mol. %) of PPh3, 130 ml of water, and 380 ml of 1,2-dimethoxyethane was refluxed for 12 h. Further on, the reaction mixture was quenched with water, solvents were evaporated. The residue was dissolved in 500 ml of dichloromethane, and this solution was washed by 500 ml of water. The organic layer was separated, the aqueous layer was additionally extracted with 100 ml of dichloromethane. The combined organic extract was dried over Na2SO4, then evaporated to dryness. The crude product isolated from the residue using flash chromatography on silica gel 60 (40-63 um, hexanes-dichloromethane=2:1, vol.) was then re-crystallized from n-hexane to give 18.5 g (43%) of a white solid.

Provenance & Evidence