Methyl iodide → 4-Bromo-2-fluoro-1-(methoxymethyl)benzene

Temperature

0 °C

The title compound was prepared according to General Method 8. To a suspension of NaH (50-60% mineral oil, 8 g, 0.33 mol) in Dry DMF (200 mL) at 0° C. was added (4-bromo-2-fluorophenyl)methanol (27 g, 0.1317 mol). The reaction mixture was stirred for 15 min at 0° C. and then warmed to and stirred at RT for 30 min. The reaction mixture was again cooled to 0° C. and MeI (15 mL, 0.1975 mol) was added drop wise. After addition was complete, the reaction mixture was warmed to room temperature and stirred for 1 h. Ice-water was added and the product was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate, and concentrated under reduced pressure to obtained 4-bromo-2-fluoro-1-(methoxymethyl)benzene (24 g).

1. customThe title compound was prepared
2. temperaturewarmed to and
3. stirringstirred at RT for 30 min
4. temperatureThe reaction mixture was again cooled to 0° C.
5. additionAfter addition
6. temperaturethe reaction mixture was warmed to room temperature
7. stirringstirred for 1 h
8. extractionthe product was extracted with ethyl acetate
9. dry with materialThe organic layer was dried over anhydrous sodium sulphate
10. concentrationconcentrated under reduced pressure

ORD record

ord-cf7e13297d3b46ebbd3de80c7ab6ca47

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08710086B2