Methanol → 1-Chloro-2-fluoro-4-methoxy-5-nitrobenzene

Temperature

0 °C

To a mixture of potassium tert-butoxide (3.0 g, 26.9 mmol) in DMF (20 mL), methanol (0.79 g, 24.8 mmol) was added at 0° C. The reaction mixture was stirred at 0° C. for 15 minutes then a solution of 1-chloro-2,4-difluoro-5-nitrobenzene (4.0 g, 20.7 mmol) in DMF (20 mL) was added at 0° C. and the reaction mass stirred for 3 hours at room temperature. Water (200 mL) was added to the reaction mixture and reaction mass was extracted with EtOAc (3×50 mL). The combined organic extracts were washed with water (80 mL), brine (80 mL), dried (Na2SO4) and concentrated under reduced pressure. The product was purified by column chromatography on neutral silica gel using 20-25% EtOAc in hexane to give the desired product (3 g, 71%) as a solid.

1. additionwas added at 0° C
2. stirringthe reaction mass stirred for 3 hours at room temperature
3. extractionwas extracted with EtOAc (3×50 mL)
4. washThe combined organic extracts were washed with water (80 mL), brine (80 mL)
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated under reduced pressure
7. customThe product was purified by column chromatography on neutral silica gel using 20-25% EtOAc in hexane

ORD record

ord-0da0360003694be6aaa3a15d4134a744

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08716287B2