Methanol → (3-Fluoro-phenoxy)-acetic acid

To a solution of ethyl 3-fluorophenoxy-acetate (2 g, 10 mmol) in 24 mL of a 1:1:1 solution of MeOH:H2O:THF is added lithium hydroxide monohydrate (2.25 g, 54 mmol). The solution is stirred for 16 hours. After this time, the solution is concentrated under reduced pressure to ⅓ of its volume. The remaining solution is acidified to pH=3 with 1N HCl (aq.). The aqueous solution is extracted with EtOAc. The organic layer is washed with a saturated solution NaCl (aq.). The organic layer is dried over MgSO4, filtered and concentrated to give the product (1.65 g, 9.7 mmol) as a white solid. 1H NMR (CDCl3, 300 MHz) δ9.8 (bs, 1H), 7.28 (m, 1H), 6.69 (m, 3H), 4.70 (s, 2H).

1. concentrationAfter this time, the solution is concentrated under reduced pressure
2. extractionThe aqueous solution is extracted with EtOAc
3. washThe organic layer is washed with a saturated solution NaCl (aq.)
4. dry with materialThe organic layer is dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-67f4880b6ec6458e953a1294e83f68f3

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07612075B2