Hexachloroethane → HCID 67350192, compound

Participants

Reaction Steps

A solution of Example 34D (3.37 g, 14.8 mmol) in THF (50 mL) was cooled to −78° C., followed by addition of LiHMDS (1M in THF, 16.3 ml, 16.3 mmol). After 0.5 hr at −78° C., hexachloroethane (3.50 g, 14.8 mmol) was added in one portion. The reaction was allowed to stir overnight with gradual warming to room temperature. The reaction was quenched with water and extracted with EtOAc. The combined organic extract was washed with water and brine, and then filtered through celite filter aid. The filtrate was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was dissolved in minimal toluene and place on silica gel (Analogix® 25×115 column) and eluted with 2 column lengths of hexanes, then 5% to 50% EtOAc/hexanes. The result was 2.20 g (57%) of the title compound as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.88 (m, 1H), 8.00-7.93 (m, 1H), 7.72-7.66 (m, 1H), 2.63 (s, 3H). MS (DCI+) m/z 263 (M+H).

Provenance & Evidence