p-Toluenesulfonic acid → HCID 58418727, compound

Participants

Reaction Steps

To a hot (110° C.) solution of 2.41 g (10.0 mmol) of 4-(bromomethyl)-1-methoxyindane in 40 ml of toluene 0.20 g of TsOH was added. This mixture was refluxed for 2 hours using a Dean-Stark head. The resulting mixture was passed through short column (4 cm) with silica gel 60 (40-63 μm), the silica gel layer was additionally washed by 20 ml of toluene. The combined elute was evaporated to dryness, the product was isolated by flash chromatography on silica gel 60 (40-63 μm, eluent: hexanes). Yield 1.98 g (95%) of the title material. Anal. calc. for C10H9Br: C, 57.44; H, 4.34. Found: C, 57.32; H, 4.41. 1H NMR (CDCl3): δ 7.40 (m, 1H, 4-H), 7.29 (m, 1H, 5-H), 7.22 (m, 1H, 6-H), 6.92 (m, 1H, 3-H), 6.63 (m, 1H, 2-H), 4.62 (s, 2H, CH2Br), 3.48 (m, 2H, 1,1′-H).

Provenance & Evidence