Allyl bromide → HCID 67540875, compound

Participants

Reaction Steps

A mixture of NaOH (0.1 g, 2.58 mmol) and 7 (0.26 g, 0.43 mmol) in DMSO (20 ml) was stirred at room temperature for 10 minutes before allylbromide (0.26 g, 2.13 mmol) was added in one portion. The mixture was stirred for another 3 hours before quenching with water followed by extraction with methylene chloride. The organic extracts were combined, washed with water and dried over MgSO4. Upon evaporating off the solvent, the crude product was purified by column chromatography on silica gel using hexane/methylene chloride 4:1 (v/v) as the eluent to yield 8 (0.14 g, 49%) as a white powder. 1H NMR (400 MHz, CDCl3, 298 K): δ(ppm) 8.52-8.44 (m, 4H), 8.21-8.19 (d, 2H), 7.87-7.84 (m, 4H), 7.52-7.42 (m, 8H), 7.27-7.25 (m, 2H), 6.15-6.02 (m, 1H), 5.28-5.12 (m, 2H), 5.02-5.01 (d, 2H), 4.16-4.14 (d, 4H), 2.50-2.40 (m, 2H), 1.04-1.03 (d, 12H).

Provenance & Evidence