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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence