Dimethyl Sulfoxide → 2,6-dibromo-8,9-dihydro-4H-cyclopenta[def]phenanthrene

Participants

Reaction Steps

2,6-dibromo-4H-cyclopenta[def]phenanthrene (2.6 g, 7.7 mmol), t-BuOK(20.8 g, 61.6 mmol), DMSO(20 ml), and HMPA(20 ml) was placed in 50 ml round bottom flask with a syringe. The mixture was stirred for 50 minutes at room temperature and cooled to 0° C. CH3l(3.75 ml, 61.6 mmol) was dropped to the mixture with a syringe and the resultant solution was stirred for 30 minutes at 0° C. Then, water(50 ml) and methylene chloride(50 ml) were added to the solution to separate an organic layer. The organic layer was purified by silica gel column chromatography to obtain compound 2(3.6 g, 80%). 1H NMR (300 MHz, CDCl3, δ): 7.98(2H, s), 7.79(2H, s), 7.73(2H, s), 1.93(m, 6H).

Provenance & Evidence