Hexachloroethane → HCID 66696688, compound

Participants

Reaction Steps

Lithium bis(trimethylsilyl)amide (1 M in tetrahydrofuran, 19.4 mL, 19.4 mmol) was added dropwise to a solution of Example 12A (4.0 g, 17.6 mmol) in tetrahydrofuran (80 mL) at −78° C. After stirring 30 min, solid hexachloroethane (8.34 g, 35.2 mmol) was added in one portion, and the reaction was allowed to gradually warm to ambient temperature. After 16 hours the reaction was quenched with half-saturated NH4Cl solution. The product was extracted with diethyl ether, and the combined organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography (Analogix Intelliflash 280; 0% to 25% ethyl acetate/hexanes; SF65-600 g column; loading with hexane/CH2Cl2) to yield 4.69 g of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 7.87 (m, 2H), 7.82 (m, 2H), 2.40 (s, 3H). MS (DCI+) m/z 262 (M+H)+.

Provenance & Evidence