Methanol → Methyl 2-chloro-5-fluorobenzoate

To a solution of 2-chloro-5-fluorobenzoic acid (22) (35.0 g, 200 mmol) in methanol (350 mL) was added cone. H2SO4 (5 mL). The mixture was heated at reflux for 24 h. Most of the solvent was evaporated, and the resulting mixture was diluted with water (300 mL). The mixture was extracted with EtOAc (150 mL×2). The combined extracts were washed with saturated NaHCO3 and brine, dried over MgSO4, and concentrated to give methyl 2-chloro-5-fluorobenzoate (23).

1. temperatureThe mixture was heated
2. temperatureat reflux for 24 h
3. customMost of the solvent was evaporated
4. additionthe resulting mixture was diluted with water (300 mL)
5. extractionThe mixture was extracted with EtOAc (150 mL×2)
6. washThe combined extracts were washed with saturated NaHCO3 and brine
7. dry with materialdried over MgSO4
8. concentrationconcentrated

ORD record

ord-4b903d616e1e43ed9e2a281491046620

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09340523B2