Phenol → Phenyl-1,1-dimethyl-1H-benzo[e]indole-2-carboxylate

Participants

Reaction Steps

200 mg of 1,1-dimethyl-1H-benzo[e]indole-2-carboxylic acid 3 (0.84 mmol) and 395 mg (4.2 mmol) phenol were dissolved in 50 mL methylene chloride. Then 188 μL (1.12 mmol) trifluorosulfonic acid anhydride were added and the reaction mixture was stirred at room temperature for 5 hours. After evaporation of the solvent under reduced pressure, the residue was taken up in methylene chloride and washed with 0.1 N NaOH and water. The organic phase was separated, dried over sodium sulfate and filtered. The solvent was removed under vacuum and the crude product was purified by preparative HPLC column chromatography (eluent: water-acetonitrile). The appropriate fractions were combined and dried by lyophilization to yield 7.5 mg of product 4.

Provenance & Evidence