Sodium Hydroxide → HCID 21883628, compound

Participants

Reaction Steps

To a stirred solution of the ester (Step 3)(0.284 g, 0.849 mmol) in THF:EtOH:H2O (7:2:1, 5 mL) was added aqueous NaOH solution (0.41 mL of 2.5 M, 1.02 mmol). After stirring 40 hours, the reaction was partially concentrated in vacuo to remove the organic solvents, diluted with H2O, washed with diethyl ether, sparged with nitrogen to remove trace diethyl ether, and acidified with concentrated HCl yielding a suspension. Vacuum filtration of the suspension yielded the title compound as a pale yellow powder (0.160 g, 23%) mp 243.3–252.4° C. 1H NMR (acetone-d6/300 MHz) 10.39 (s, 1H), 7.98 (s, 1H), 7.88 (d, 1H, J=2.6 Hz), 7.75 (d, 1H, J=2.6 Hz), 6.08 (q, 1H, J=6.9 Hz). FABLRMS m/z 307 (M+H). ESHRMS m/z 304.9839 (M−H, Calc'd 304.9828). Anal. Calc'd for C12H6Cl1F3O4: C, 47.01; H, 1.97. Found: C, 46.64; H,1.86.

Provenance & Evidence