Iodoethane → o-Fluorophenatole

2-fluorophenol 4a (6.7 g, 60 mmol) was dissolved in 66 mL acetone, followed by addition of ethyl iodide (6.3 mL, 78 mmol) and potassium carbonate (12.4 g, 90 mmol). The reaction mixture was refluxed in an oil bath for 5 hours. Thereafter, the reaction mixture was concentrated under reduced pressure and partitioned after 100 mL ethyl acetate and 60 mL water were added. The aqueous phase was extracted with ethyl acetate (30 mL×2) and the organic extract was combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound 1-ethoxy-2-fluoro-benzene 4b (6.9 g, red grease), yield: 82.1%. MS m/z (ESI): 280.2 [2M+1].

1. temperatureThe reaction mixture was refluxed in an oil bath for 5 hours
2. concentrationThereafter, the reaction mixture was concentrated under reduced pressure
3. custompartitioned after 100 mL ethyl acetate and 60 mL water
4. additionwere added
5. extractionThe aqueous phase was extracted with ethyl acetate (30 mL×2)
6. extractionthe organic extract
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-5b89a3650932438aa3a578420c7f48b8

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609622B2