Dimethyl Sulfate → Methyl 2-fluoro-6-iodobenzoate

Temperature

50 °C

To a 200 mL round-bottomed flask were added 2-fluoro-6-iodo-benzoic acid (7.5 g, 28.2 mmol), LiOH.H2O (1.42 g, 33.8 mmol), and THF (100 mL). The resulting mixture was warmed to 50° C. and stirred for 2 h. Dimethyl sulfate (4.03 mL, 42.3 mmol) was then added and the mixture was warmed to 65° C. After 2 h, the mixture was cooled to room temperature and NH4Cl(aq) (50 mL, 13 wt % solution) was added. The two resulting layers were thoroughly mixed and then separated. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to a light brown oil (7.79 g, 99% yield). 1H NMR (400 MHz, CDCl3): 7.68-7.60 (m, 1H), 7.15-7.06 (m, 2H), 3.98 (s, 3H).

1. temperaturethe mixture was warmed to 65° C
2. waitAfter 2 h
3. temperaturethe mixture was cooled to room temperature
4. additionThe two resulting layers were thoroughly mixed
5. customseparated
6. dry with materialThe organic layer was dried over MgSO4
7. filtrationfiltered

ORD record

ord-ba4c3e68549b4aebb9ecf629eb018657

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653263B2