Methyl iodide → 3-Fluoro-4-nitroanisole

A 2 L round bottom flask equipped with a stir bar and reflux condenser was charged with acetonitrile (1 L), K2CO3 (263 g, 1.9 mol) and 4-hydroxy-2-fluoro-1-nitrobenzene (100 g, 0.64 mol). Methyl iodide (271 g, 1.9 mol) was added to the reaction mixture and heated at reflux temperatures with vigorous stirring for 5 h. The acetonitrile was removed and ethyl acetate (1 L) and H2O (700 mL) were added. The heterogeneous mixture was transferred to a separatory funnel where the aqueous phase was separated and re-extracted with ethyl acetate (2×200 mL). The organic phases were combined and washed with H2O (2×500 mL), brine (500 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give the desired product as a slightly yellow solid (107 g, 98%).

1. customA 2 L round bottom flask equipped with a stir bar
2. temperaturereflux condenser
3. temperatureheated
4. temperatureat reflux temperatures
5. customThe acetonitrile was removed
6. additionethyl acetate (1 L) and H2O (700 mL) were added
7. customThe heterogeneous mixture was transferred to a separatory funnel
8. customwhere the aqueous phase was separated
9. extractionre-extracted with ethyl acetate (2×200 mL)
10. washwashed with H2O (2×500 mL), brine (500 mL)
11. dry with materialdried over MgSO4
12. filtrationfiltered
13. concentrationconcentrated under reduced pressure

ORD record

ord-ccc291293e564a4ab7bf257a4fa2289d

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08618155B2