Hydrochloric Acid → 1-Chloro-2-ethynylbenzene

Participants

Reaction Conditions

Reaction Steps

Potassium hydroxide (77.5 g, 1.38 mol) was added in 4 portions to a stirred solution of (2-chlorophenylethynyl)-trimethylsilane (95.0 g, 0.46 mol) in methanol (250 ml) at 0° C. The mixture was stirred at 0° C. until the reaction was complete (by tlc 1:1 ethyl acetate:hexane). The mixture was neutralised by the addition of 10% hydrochloric acid and the product was extracted into dichloromethane (2×150 ml). The combined extracts were dried (MgSO4) and evaporated in vacuo. The residual oil was purified by short path distillation (Kugelrohr) to give 1-chloro-2-ethynylbenzene (41.23 g) as a clear oil. B.pt. 38° C./10 mBar. 250 MHz 1H-NMR (CDCl3) δ (ppm): 3.25 (s, 1H)(CH), 7.1-7.5 (m, 4H) (ArH); GC purity 89%, GC retention time 2.67 min.

Provenance & Evidence