Water → (3-chloro-4-fluorophenoxy)acetic acid

To a stirring solution of finely ground KOH (1.2 g, 20.4 mmol) in DMSO (6 mL) was added 3-chloro-4-fluorophenol (1.0 g, 6.8 mmol). The mixture was stirred for 10 minutes at RT, then cooled to 0° C. Methyl bromoacetate (1.25 g, 8.2 mmol) was added, and the reaction was slowly warmed to RT and stirred overnight. H2O (10 mL) and MeOH (10 mL) were added to the mixture, and the reaction was stirred for 1 h. After removing MeOH under reduced pressure, H2O (100 mL) and Et2O (50 mL) were added, and the layers were separated. The aqueous phase was acidified to pH 2 with an aqueous concentrated HCl solution and extracted with CH2Cl2 (200 mL). The organic layer was dried over MgSO4, filtered, concentrated, and dried to give 2-(3-chloro-4-fluorophenoxy)acetic acid as a white solid (1.1 g, 79%). 1H NMR (400 MHz, CDCl3) δ 7.10 (t, J=8.8 Hz, 1H), 7.01-6.98 (m, 1H), 6.84-6.80 (m, 1H), 4.68 (s, 2H).

1. temperaturecooled to 0° C
2. temperaturethe reaction was slowly warmed to RT
3. stirringstirred overnight
4. stirringthe reaction was stirred for 1 h
5. customAfter removing MeOH under reduced pressure, H2O (100 mL) and Et2O (50 mL)
6. additionwere added
7. customthe layers were separated
8. extractionextracted with CH2Cl2 (200 mL)
9. dry with materialThe organic layer was dried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated
12. customdried

ORD record

ord-cc67523c58214243b52efd6175feb43e

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08586589B2