Iodine → HCID 90413796, compound

Participants

Reaction Conditions

Reaction Steps

Sec-Butyllithium (1.4 M in cyclohexane; 6.1 mL, 8.5 mmol) was added to dry tetrahydrofuran (15 mL) which had been pre-cooled to −40° C. The solution was cooled to −75° C., treated with 2,2,5-trifluorobenzo[d][1,3]dioxole (1.5 g, 8.5 mmol) and stirred at this temperature for 90 min. This solution was rapidly transferred via cannula into a stirred solution of iodine (2.8 g, 11 mmol) in tetrahydrofuran (25 mL), and the mixture was cooled to −75° C. The mixture was stirred for 1 h during which time the temperature rose to −20° C. The reaction was quenched by addition of saturated NH4Cl (10 mL) and then combined with 10% NaHSO3 (15 mL) and ethyl acetate (30 mL). The organic phase was washed with saturated NaCl (10 mL), dried (Na2SO4) and evaporated. The material was purified by flash chromatography with hexane to give the title compound as a clear liquid (1.5 g, 58%): 1H NMR (400 MHz, CDCl3) δ 6.97 (dd, J=8.8, 4.0 Hz, 1H), 6.81 (dd, J=11.7, 5.4 Hz, 1H); 19F NMR (376 MHz, CDCl3) δ −49.06, −103.15; EIMS m/z 302.

Provenance & Evidence