Methyl iodide → Methyl 4-bromo-5-fluoro-2-nitrobenzoate

To a stirred solution of 4-bromo-5-fluoro-2-nitrobenzoic acid (Ark Pharm, 5.387 g, 20.40 mmol) in DMF (80.0 mL) at 0° C. was added potassium carbonate (5.870 g, 42.47 mmol), followed by methyl iodide (8.789 g, 61.92 mmol). After stirring at 0° C. for 15 min., the reaction was heated to 40° C. for 2 h. The mixture was filtered and concentrated. The residue was dissolved in EtOAc (150 mL), washed with water (2×100 mL), brine (100 mL), dried over Na2SO4, and concentrated under reduced pressure. The resulting residue was purified by flash chromatography on silica gel (0-50% EtOAc in hexanes) to give the sub-title compound as a pale yellow oil (5.348 g, 94%). LCMS calc. for C8H6BrFNO4 (M+H)+: m/z=277.9. found no ionization.

1. temperaturethe reaction was heated to 40° C. for 2 h
2. filtrationThe mixture was filtered
3. concentrationconcentrated
4. dissolutionThe residue was dissolved in EtOAc (150 mL)
5. washwashed with water (2×100 mL), brine (100 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated under reduced pressure
8. customThe resulting residue was purified by flash chromatography on silica gel (0-50% EtOAc in hexanes)

ORD-Eintrag

ord-aa6cf5100eb64b44b5dbf16d7a018040

Quelldatensatz

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09278950B2