Hexachloroethane → HCID 68933583, compound

Participants

Reaction Steps

Add 2.2 equiv of n-BuLi-hexanes dropwise to a solution of 3-(9,10-dihydro-1-thia-benzo[f]azulen-4-ylidenemethyl)-phenylamine in THF (0.1 M) at 0° C. under Ar. Stir the resultant dark solution for 1 h before adding 2.5 equiv of hexachloroethane in THF. Stir for 2 h, quench with excess water, and acidify to neutral pH. Extract the aqueous layer with diethyl ether (3×) and then dry (MgSO4) and concentrate the combined organic layers under reduced pressure. Purify the crude residue by column chromatography (0% to 2% to 20% EtOAc:hexanes) to give title compound as an oil (22%) along with recovered starting material: HPLC (ISO80-20A) t=1.903 (90%). MS (APCI): 338 (M+1).

Provenance & Evidence