Dichloromethane → 5-Fluoro-2-nitroanisole

5-Fluoro-2-nitrophenol (3.14 g; 20 mmol) and potassium carbonate (2.76 g; 20 mmol) are place in a round bottom flask and are flushed with argon. Dry dimethylformamide (60 mL) is added followed by dimethylsulfate (3.8 mL; 40 mmol). The reaction is stirred for 2 days at room temperature. Dichloromethane (120 mL) and water (60 mL) are then added. The aqueous phase is extracted with dichloromethane (100 mL) and the combined organic layers are washed three times with aq. sat. sodium hydrogencarbonate (50 mL), twice with aq. 1N hydrochloric acid (50 mL) and with brine (50 mL). The organic layer is then dried over magnesium sulfate and is concentrated under reduced pressure. The desired product is isolated in the presence of dimethylformamide (4.39 g).

1. customare flushed with argon
2. additionDry dimethylformamide (60 mL) is added
3. extractionThe aqueous phase is extracted with dichloromethane (100 mL)
4. washthe combined organic layers are washed three times with aq. sat. sodium hydrogencarbonate (50 mL)
5. dry with materialThe organic layer is then dried over magnesium sulfate
6. concentrationis concentrated under reduced pressure

ORD record

ord-a36ecfb87e914d0eb70b24ed3f15517a

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096524B2