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. CH3I (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