Hydrochloric Acid → HCID 65203823, compound

Participants

Reaction Conditions

Reaction Steps

Into a 2000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of argon was placed ethyl 4-(4-bromo-3-fluorophenoxy)butanoate (80.6 g, 264.14 mmol, 1.00 equiv), LiOH (12.7 g, 530.27 mmol, 2.00 equiv), tetrahydrofuran (250 mL), and water (240 mL). The resulting solution was stirred at 50° C. overnight, cooled to 0° C. with a water/ice bath, adjusted to pH=3-4 with hydrochloric acid (2 N) and extracted with 3×100 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was triturated in 30 mL of EA to afford 50 g (68%) of 4-(4-bromo-3-fluorophenoxy)butanoic acid as a white solid.

Provenance & Evidence