Water → 6-tert-Butyl-5-methoxy-2-methyl-4-phenylindan-1-one

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Reaction Steps

To a mixture of 46.7 g (0.150 mol) of 4-bromo-6-tert-butyl-5-methoxy-2-methylindan-1-one, 44.5 g (0.420 mol) of Na2CO3, 22.0 g (0.180 mol) of PhB(OH)2, 570 ml of DME, and 195 ml of water 0.674 g (3.0 mmol) of Pd(OAc)2 and 1.58 g (6.00 mmol) of PPh3 were added. The resulting mixture was refluxed for 12 h, cooled to room temperature, and then DME was evaporated on Rotavap. To the residue 1 liter of cold water was added, and the crude product was extracted with 3×300 ml of dichloromethane. The combined organic extract was dried over K2CO3 and then evaporated to dryness. The residue after evaporation was extracted with hot hexane (500 ml, then 3×250 ml) and this extracts while hot were passed through a short pad of silicagel, evaporated on Rotavap to yield 45.1 g (98%) of 6-tert-butyl-5-methoxy-2-methyl-4-phenylindan-1-one as a slightly yellowish crystalline solid which was further used without an additional purification.

Provenance & Evidence