Hexachloroethane → HCID 66696652, compound

Participants

Reaction Steps

LiHMDS (1 M in THF, 4.4 mL, 4.4 mmol) was added dropwise via syringe to a solution of Example 29A (1.03 g, 4.02 mmol) in THF (20 mL) at −78° C. After 30 min solid hexachloroethane (1.90 g, 8.04 mmol) was added in one portion and the reaction mixture was allowed to gradually warm to ambient temperature over 16 hr. The reaction was diluted with Et2O and quenched with half-saturated aqueous NH4Cl solution. The separated aqueous phase was extracted with Et2O, and the combined organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Flash chromatography (Analogix® Intelliflash 280™; 0% to 15% EtOAc/hexanes eluant; SF25-120 g column) afforded 1.07 g (92%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 7.84 (dd, J=8.4, 7.4 1H), 7.57 (dd, J=9.9, 2.0 1H), 7.39 (dd, J=8.5, 2.0 1H), 2.36 (s, 3H). MS (DCI+) m/z 290/292 (M+H).

Provenance & Evidence