Hydrochloric Acid → Methyl 5-bromo-2,4-difluorobenzoate

Temperature

95 °C

Concentrated hydrochloric acid (10.4 mL, 127 mmol) was slowly added to a mixture of 5-bromo-2,4-difluorobenzoic acid (0.999 g, 4.21 mmol) in methanol (26 mL). The mixture was heated at 95° C. for 18 hours. The reaction was cooled and then concentrated in vacuo. The residue was diluted with water (50 mL) and extracted with EtOAc (3×50 mL). The combined organic extract was washed with brine (2×50 mL), dried over sodium sulfate, filtered and concentrated in vacuo to afford a brown oil (0.847 g). The crude product was purified by silica gel chromatography (Biotage®, 100 g SNAP cartridge, 5 to 50% EtOAc in Heptane) to afford the title compound as clear crystalline solid (0.544 g).

1. temperatureThe reaction was cooled
2. concentrationconcentrated in vacuo
3. additionThe residue was diluted with water (50 mL)
4. extractionextracted with EtOAc (3×50 mL)
5. extractionThe combined organic extract
6. washwas washed with brine (2×50 mL)
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-96e186932e354987886a71384dd07276

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772343B2