Methanol → HCID 86687422, compound

Participants

Reaction Conditions

Reaction Steps

A round bottom flask was charged with 6-bromo-2h-isoquinolin-1-one (5.0 g, 22.32 mmol) and 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor®) (9.49 g, 26.8 mmol, Air Products, Allentown, Pa.). Methanol (55.8 ml) and acetonitrile (55.8 ml) were added and the reaction was heated to 50° C. and stirred for one hour. The reaction was concentrated, dissolved in DCE (110 mL), and POCl3 (4.16 ml, 44.6 mmol) was added. The reaction was stirred at 50° C. for one hour. The reaction was quenched into ice water and extracted with ethyl acetate. The combined organic layers were dried with sodium sulfate, filtered, and concentrated to afford crude 6-bromo-4-fluoroisoquinolin-1(2H)-one as a light pink solid. (ESI) 242.1 (M+H)+.

Provenance & Evidence