Toluene → 7-(bromomethyl)-2-methyl-1H-indene

Participants

Reaction Steps

To a solution of 37.5 g (0.147 mol) of 4-(bromomethyl)-1-methoxy-2-methylindane in 600 ml of toluene 3.12 g (16.4 mmol) of TsOH was added at 110° C. This mixture was refluxed with Dean-Stark trap within 12 min and then passed through short column with Silica Gel 60 (40-63 um, d 90 mm, l 80 mm). The Silica Gel layer was additionally washed by 500 ml of toluene. The combined elute was evaporated to dryness. The product was isolated by flash chromatography on short column with Silica Gel 60 (40-63 um, d 90 mm, l 80 mm; eluent: hexanes). Yield 33.2 g (97%).

Provenance & Evidence