1H-Indene, 2-methyl- → 7-(2-bromoethyl)-2-methyl-1H-indene

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Reaction Steps

To a solution of 1.30 g (10 mmol) of 2-methyl-1H-indene in 90 ml of ether 4.0 ml of 2.5 M (10 mmol) n-BuLi in hexanes was added at 0° C. This mixture was stirred for 2 h at room temperature, and then a solution of 2.23 g (10 mmol) of 7-(bromomethyl)-2-methyl-1H-indene in 15 ml of THF was added dropwise at vigorous stirring for 10 min at −80° C. The resulting mixture was stirred for 12 h at room temperature, and then 1 ml of water was added. This mixture was evaporated to dryness, and 100 ml of water was added. The crude product was extracted with 3×50 ml of dichloromethane. The combined organic extract was dried over Na2SO4 and evaporated to dryness. The product was isolated by flash chromatography using a short column with Silica Gel 60 (40-63 um, d 60 mm, l 70 mm; eluent: hexanes. Yield 2.50 g (92%) of 2-methyl-1-[(2-methyl-1H-inden-7-yl)methyl]-1H-indene.

Provenance & Evidence