Potassium Carbonate → Butanoic acid, 4-(4-bromo-3-fluorophenoxy)-, ethyl ester

Temperature

56 °C

Into a 2000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of argon was placed 4-bromo-3-fluorophenol (50 g, 261.78 mmol, 1.00 equiv), acetone (500 mL), NaI (2.8 g, 0.07 equiv), potassium carbonate (54.2 g, 392.16 mmol, 1.50 equiv), and ethyl 4-bromobutanoate (61.3 g, 314.27 mmol, 1.20 equiv). The resulting solution was stirred at 56° C. overnight. The solids were filtered out and the filtrate was concentrated under vacuum. The residue was dissolved in 1000 mL of EA and the resulting mixture was washed with 2×100 mL of sodium hydroxide (1 N) and 3×100 mL, of water. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to afford 80.6 g (crude) of ethyl 4-(4-bromo-3-fluorophenoxy)butanoate as a light yellow oil.

1. customInto a 2000-mL 4-necked round-bottom flask purged
2. temperaturemaintained with an inert atmosphere of argon
3. filtrationThe solids were filtered out
4. concentrationthe filtrate was concentrated under vacuum
5. dissolutionThe residue was dissolved in 1000 mL of EA
6. washthe resulting mixture was washed with 2×100 mL of sodium hydroxide (1 N) and 3×100 mL, of water
7. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
8. concentrationconcentrated under vacuum

ORD record

ord-361afcae56044c0aa5c0f8073870e614

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034866B2