Carbon Dioxide → 2-Fluoro-6-iodo-3-methylbenzoic acid

Temperature

-78 °C

A −78° C. solution of 2-fluoro-4-iodo-1-methylbenzene (25 g, 105.9 mmol) in THF (200 mL) was treated dropwise with LDA (2M solution in THF, 58.5 mL, 116 mmol), stirred at −78° C. for 1 hour, treated with excess powdered dry ice, stirred at −78° C. for 30 minutes, and warmed to room temperature gradually over about 18 hours. The mixture was concentrated and the residue was partitioned between 4N NaOH and diethyl ether. The aqueous phase was adjusted to pH 2 with 2N HCl and extracted three times with ethyl acetate. The combined extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated to provide 19.4 g (66% yield) of the desired product. MS (ESI(+)) m/e 279 (M+H)+.

1. stirringstirred at −78° C. for 30 minutes
2. temperaturewarmed to room temperature gradually over about 18 hours
3. concentrationThe mixture was concentrated
4. customthe residue was partitioned between 4N NaOH and diethyl ether
5. extractionextracted three times with ethyl acetate
6. washThe combined extracts were washed with water and brine
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-2b872170636b400da71a27f141d8dbb3

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08940778B2