Hexachloroethane → HCID 66696594, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Example 57A (7.32 g, 30.6 mmol) in THF (150 mL) was cooled to −78° C., and treated carefully with LiHMDS (1 M in THF, 37 mL, 37 mmol). The mixture was stirred at −78° C. for 20 minutes, then was treated all at once with hexachloroethane (14.5 g, 61.2 mmol). The flask was removed from the cold bath, and the reaction mixture was stirred overnight at room temperature. After this time, the mixture was diluted with Et2O and washed with saturated NH4Cl solution and water, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was chromatographed on silica gel (100% hexane, then 0% to 20% EtOAc/hexane) to afford 7.44 g (89%) of the title compound as a pale yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.68 (d, J=2.4, 1H), 7.87 (dd, J=8.4, 2.4, 1H), 7.48 (dd, J=8.7, 0.7, 1H), 2.57 (s, 3H). MS (DCI+) m/z 273/275 (M+H).

Provenance & Evidence