Carbon Dioxide → 5-Chloro-2-(trifluoromethoxy)benzoic acid

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A 1.6 M solution of butyllithium in hexanes (26.5 mmol, 16.5 mL) was added to a 0° C. solution of diisopropylamine (2.65 g, 26.5 mmol) in tetrahydrofuran (50 mL). The solution was cooled to −100° C., and 1-chloro-4-(trifluoromethoxy)benzene (Matrix) (5.0 g, 26.5 mmol) was added. After 2 h at −100° C., the mixture was poured onto an excess of freshly crushed dry ice. After evaporation of the volatiles, the residue was dissolved in a 1 M aqueous solution (50 mL) of sodium hydroxide, washed with diethyl ether (2×15 mL), and acidified to pH 1 by the addition of concentrated hydrochloric acid (7 mL). The aqueous layers were extracted with diethyl ether (3×30 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated to afford the title product. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.54 (dd, J=8.8, 1.0 Hz, 1H) 7.78 (dd, J=8.8, 2.7 Hz, 1H) 7.92 (d, J=2.7 Hz, 1H).

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