Hexachloroethane → HCID 66696664, compound

Participants

Reaction Conditions

Reaction Steps

LiHMDS (1.0 M in THF, 24 mL, 24 mmol) was added to a solution of Example 54A (4.90 g, 21.9 mmol) in THF (73 mL) at −78° C. The reaction was stirred at −78° C. for 30 min, and then solid hexachloroethane (5.20 g, 21.9 mmol) was added in one portion. The reaction was allowed to stir overnight while warming to room temperature. The reaction was quenched with water and the product extracted with EtOAc. The combined organic extract was washed with water and brine, and filtered through celite. The filtrate was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was dissolved in toluene and loaded on silica gel (Analogix® 25×115 column), and eluted with 2 column lengths of hexanes then 5% to 50% EtOAc/hexanes. The result was 4.1 g (73%) of the title compound as a pale yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.63 (d, J=8.5, 2H), 7.58 (d, J=8.7, 2H), 6.68 (t, J=56.5, 1H), 2.77 (q, J=7.5, 2H), 1.31 (t, J=7.5, 3H). MS (DCI+) m/z 258 (M+H).

Provenance & Evidence