Carbon Dioxide → 5-Bromo-2,3,4-trifluorobenzoic acid

Temperatur

0 °C

To a solution of iPr2NH (56.8 mmol, 8 ml) in THF (50 ml) at −78° C. was added dropwise a solution of nBuLi (1.6M in hexane, 56.8 ml, 35.5 mmol). The dry ice bath was removed and the mixture was stirred at 0° C. for ˜15 min. The mixture is transferred via cannula to a solution of 1-bromo-2,3,4-trifluorobenzene (47.4 mmol, 10 g) in THF (50 ml) cooled at −78° C. The orange solution was stirred at −78° C. for 1 h, then transferred, via cannula, to freshly grinded dry CO2. The reaction was warmed up to room temperature and stirred overnight. The reaction mixture was cooled at 0° C., quenched with 10% HCl (300 ml), extracted with ether (100 ml×3), dry over MgSO4 and concentrated under reduced pressure to obtain (10.6 g, 88%) of the title compound.

1. customThe dry ice bath was removed
2. temperaturecooled at −78° C
3. stirringThe orange solution was stirred at −78° C. for 1 h
4. temperatureThe reaction was warmed up to room temperature
5. stirringstirred overnight
6. temperatureThe reaction mixture was cooled at 0° C.
7. customquenched with 10% HCl (300 ml)
8. extractionextracted with ether (100 ml×3)
9. dry with materialdry over MgSO4
10. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-d6a4fcbb976440079bb1606a45ae0388

Quelldatensatz

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08063049B2