Dichloromethane → 8-Fluoro-6-methylphenanthridine

Participants

Reaction Conditions

Reaction Steps

1H NMR and TLC and no starting material was present (2-iodoaniline). 2-Acetyl-4-fluorophenyl trifluoromethanesulfonate (7.9 g, 28 mmol) was added to the reaction mixture, along with aqueous sodium carbonate (2 M, 61 mL, 122 mmol) and additional [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (1.0 g, 1.22 mmol) and N,N-dimethylformamide (50 mL). The reaction mixture was degassed several times and heated at 85° C. for 18 hours. The mixture was cooled to room temperature and poured into water (250 mL). The suspension was extracted with diethyl ether (2×250 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to give a brown oil. Purification by column chromatography (1:4 ethyl acetate:hexane) gave the product as a pale yellow solid (1.33 g, 27% ).

Provenance & Evidence