Hexachloroethane → HCID 66696615, compound

Participants

Reaction Steps

A solution of Example 30A (1.56 g, 8.16 mmol) in THF (36 mL) was cooled to −78° C., followed by dropwise addition of LiHMDS (1 M in THF, 10.2 mL, 10.2 mmol). The reaction was stirred 30 min and then hexachloroethane (3.86 g, 16.3 mmol) was added in one portion. The reaction was allowed to slowly warm to room temperature and stir over the weekend. The reaction was then quenched with 50 mL of 1:1 water:saturated aqueous NH4Cl solution, and extracted with Et2O (2×). The combined organic layer was dried with MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel (Analogix® SF40-80 g column) eluting with 7% EtOAc/hexanes to yield 1.71 g (93%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 7.43 (dd, J=11.9, 4.4 1H), 7.35-7.29 (m, 2H), 2.34 (s, 3H), 2.27 (d, J=1.9, 3H). MS (DCI+) m/z 226 (M+H).

Provenance & Evidence