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, 3 H), 7.14 (td, J=8.34, 4.80 Hz, 1 H), 7.35 (ddd, J=10.74, 8.34, 1.64 Hz, 1 H), 7.58 (dt, J=8.27, 1.55 Hz, 1 H).

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-cc76373ebe254450a34dfcf1d9e305a0

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096624B2