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

温度

-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レコード

ord-911c3cb547b0486b839dcebae617c252

出典データセット

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08642776B2