Methanol → Benzoic acid, 3-fluoro-, methyl ester

Temperature

0 °C

A solution of 3-fluorobenzoic acid (3.0 g, 21.4 mmol) in methanol (71 mL) at 0° C. is treated dropwise with thionyl chloride (3.1 mL, 42.8 mmol). The solution is stirred for 15 min at 0° C., 2.5 h at room temperature, and 2 h at 50° C. The reaction is concentrated in vacuo and the residue dissolved in ethyl acetate (150 mL). The organic solution is washed with saturated aqueous sodium bicarbonate (2×100 mL), brine (100 mL), and dried over sodium sulfate. The solution is decanted and concentrated to yield the title compound, 2.61 g (79%), as a clear, colorless oil.

1. custom2 h
2. customat 50° C
3. concentrationThe reaction is concentrated in vacuo
4. dissolutionthe residue dissolved in ethyl acetate (150 mL)
5. washThe organic solution is washed with saturated aqueous sodium bicarbonate (2×100 mL), brine (100 mL)
6. dry with materialdried over sodium sulfate
7. customThe solution is decanted
8. concentrationconcentrated

ORD record

ord-07b35be662464431ac6ab56315a55875

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07087626B2