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

Participants

Reaction Steps

2-bromo-4H-cyclopenta[def]phenanthrene (2.6 g, 7.7 mmol), t-BuOH (20.8 g, 61.6 mmol), DMSO (20 ml), and HMPA (20 ml) were put into a 50 ml round bottom flask using a syringe. The reaction mixture was stirred at room temperature for 50 minutes and cooled to 0° C. Then, CH3I (3.75 ml, 61.6 mmol) was dropwise added to the flask using a syringe at 0° C. and the reaction mixture was stirred at 0° C. for 30 minutes. Then, water (50 ml) and methylene chloride (50 ml) were added to the flask to separate an organic phase. The organic phase was purified by silica gel column chromatography to give a compound 2 (3.6 g, 80%). 1H NMR (300 MHz, CDCl3, δ): 7.98 (2H, s), 7.79 (2H, s), 7.73 (2H, s), 6.94 (dd, 1H), 1.93 (m, 6H).

Provenance & Evidence