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

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Reaction Steps

A mixture of 31.1 g (100 mmol) of 4-bromo-6-tertbutyl-5-methoxy-2-methylindanone, 25.0 g (140 mmol) of 4-tert-butylphenylboronic acid, 29.4 g (280 mmol) of Na2CO3, 1.35 g (6.00 mmol, 6 mol. %) of Pd(OAc)2, and 3.15 g (12.0 mmol, 12 mol. %) of PPh3 in 130 ml of water and 380 ml of DME was refluxed for 6 h in argon atmosphere. The formed mixture was evaporated to dryness. To the residue 500 ml of dichloromethane and 500 ml of water were added. The organic layer was separated, the aqueous layer was additionally extracted with 100 ml of dichloromethane. The combined organic extract was dried over Na2SO4, evaporated to dryness, and the crude product was isolated using flash chromatography on silica gel 60 (40-63 um; eluent: hexanes-dichloromethane=2:1, vol.). This crude product was recrystallized from n-hexane to give 29.1 g (81%) of a white solid.

Provenance & Evidence