Hexachloroethane → HCID 66696632, compound

Participants

Reaction Steps

LiHMDS (1.0 M in THF, 13 ml, 13 mmol) was added slowly via syringe to a solution of Example 45B (3.04 g, 11.6 mmol) in THF (50 mL) at −78° C. The solution was stirred 45 min, and then solid hexachloroethane (4.13 g, 17.4 mmol) was added in one portion. The reaction was allowed to proceed for 12 hr with gradual warming to ambient temperature. The reaction was quenched with half-saturated aq NH4Cl solution, and the product was extracted with Et2O. The combined organic extract was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (Analogix® Intelliflash 280™; 0% to 20% EtOAc/hexanes eluant; SF40-150 g column) to afford 3.02 g (88%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 7.97 (d, J=8.4, 1H), 7.86 (s, 1H), 7.75 (d, J=8.3, 1H), 2.42 (s, 3H). MS (DCI+) m/z 296 (M+H).

Provenance & Evidence