4-Iodoanisole → 1,2-Bis(4-methoxyphenyl)ethyne

Participants

Reaction Conditions

Reaction Steps

To the solution of 4-methoxy-phenyl-acetylene (10 g, 0.075 mol) and 4-iodo-anisole (17.65 g, 1.0 eq.) in diethylamine (150 mL) was added Pd(PPh3)2Cl2 (2.65 g, 0.05 eq.) and the reaction mixture was stirred for 30 min at 0° C. To the reaction mixture was then added Cul (1.43 g, 0.1 eq.) and the mixture was stirred at 6 h at 0˜25° C. The reaction mixture was then concentrated and partitioned between ethyl acetate/H2O (200/600 mL). The organic layer was separated, dried and purified on SiO2 (1˜5% ethyl acetate/hexane) to yield 1,2-di(4-methoxy-phenyl)-acetylene.

Provenance & Evidence