Sodium Hydroxide → 8-Fluoro-2-methylquinolin-7-ol

Participants

Reaction Steps

A solution of 8-fluoro-7-methoxy-2-methylquinoline (0.57 g, 2.96 mmol) was stirred in dichloromethane (5 mL) and treated with a 1M solution of BBr3 in dichloromethane (15 mL). The resulting mixture was heated at reflux for 16 hours, then poured into crushed ice and basified with a 6N NaOH solution to pH 14. The organic layer was separated and the aqueous layer was further extracted with dichloromethane. The organic layer was pH adjusted to 6 with aqueous 6N HCl and extracted with ethyl acetate. The combined organic extracts were dried (MgSO4), filtered and concentrated under reduced pressure to afford 8-fluoro-2-methylquinolin-7-ol in quantitative yield.

Provenance & Evidence