Sodium Hydroxide → 5-Chloro-2-fluoro-4-methylbenzoic acid

To a stirred solution of methyl 5-chloro-2-fluoro-4-methylbenzoate (Preparation 240, 340 mg, 1.68 mmol) in dioxane/water (5:1, 12 mL) was added an aqueous sodium hydroxide solution (5 M, 1.63 mL, 8.39 mmol). The reaction mixture was stirred at room temperature for 18 hours and then evaporated in vacuo. The resulting residue was suspended in water and extracted with diethyl ether (3×20 mL). The aqueous layer was separated, cooled in an ice bath, acidified with aqueous hydrochloric acid (6 M) and then extracted with EtOAc (30 mL). The organic phase was washed with brine (2×20 mL), dried over sodium sulphate, filtered and evaporated in vacuo to yield the title compound as a white solid (266 mg, 84%).

1. customevaporated in vacuo
2. extractionextracted with diethyl ether (3×20 mL)
3. customThe aqueous layer was separated
4. temperaturecooled in an ice bath
5. extractionextracted with EtOAc (30 mL)
6. washThe organic phase was washed with brine (2×20 mL)
7. dry with materialdried over sodium sulphate
8. filtrationfiltered
9. customevaporated in vacuo

ORD record

ord-5c798975f37f43dd9d5a587ae73f8d72

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592629B2