Hydrochloric Acid → (3-Fluoro-phenoxy)-acetic acid

Temperature

80 °C

To a stirred mixture of 3-fluorophenol (100 mg, 0.893 mmol) in MeCN (5 mL) was added ethyl bromoacetate (222 mg, 1.34 mmol) and K2CO3 (369 mg, 2.68 mmol). The mixture was stirred at 80° C. for 4 hours. The mixture was then filtered and the filtrate concentrated. NaOH (71 mg, 1.79 mmol) and water:EtOH (1:1, 10 mL) was added to the residue and the mixture stirred at 50° C. for 4 hours. The mixture was acidified by adding 1M HCl, and then extracted with ethyl acetate (2×30 mL). The combined extracts were washed with brine (30 mL), dried over anhydrous Na2SO4 and concentrated. The residue was directly for the next step. LCMS (m/z): 171.0 (M+1).

1. filtrationThe mixture was then filtered
2. concentrationthe filtrate concentrated
3. stirringthe mixture stirred at 50° C. for 4 hours
4. extractionextracted with ethyl acetate (2×30 mL)
5. washThe combined extracts were washed with brine (30 mL)
6. dry with materialdried over anhydrous Na2SO4
7. concentrationconcentrated

ORD record

ord-4674fd156493468a9b062f9b37f75229

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08940726B2