Methyl iodide → 2-Fluoro-6-nitroanisole

A solution of 2-fluoro-6-nitrophenol (10.0 g, 63.6 mmol) in DMF (25.0 mL) was charged with methyl iodide (5.94 mL, 95.5 mmol) and potassium carbonate (13.2 g, 95.5 mmol). The reaction mixture was stirred at rt for 16 h. The reaction was quenched with water (30 mL) and extracted with EtOAc (30 mL). The organic layer was washed with water (25 mL), washed with Brine (25 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to yield a brown oil, 11.0 g (101% yield). 1H NMR (CDCl3, 400 MHz): δ=4.08 (d, J=2.02 Hz, 3H), 7.14 (td, J=8.34, 4.80 Hz, 1H), 7.35 (ddd, J=10.74, 8.34, 1.64 Hz, 1H), 7.58 (dt, J=8.27, 1.55 Hz, 1H).

1. customThe reaction was quenched with water (30 mL)
2. extractionextracted with EtOAc (30 mL)
3. washThe organic layer was washed with water (25 mL)
4. washwashed with Brine (25 mL)
5. dry with materialdried over anhydrous Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customto yield a brown oil, 11.0 g (101% yield)

ORD record

ord-0376f00ada7145cbb2a218ea98e605ce

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399433B2