2-Methoxyethanol → 1-Iodo-4-(2-methoxyethoxy)benzene

Participants

Reaction Steps

Triphenylphosphine (2.8 g, 10.7 mmol) was added to an ice-cold solution of 4-iodophenol (2.2 g, 10.0 mmol) and 2-methoxyethanol (0.79 ml, 10.0 mmol) in tetrahydrofuran (10 ml). A solution of diethyl azodicarboxylate (1.88 ml, 11.5 mmol) in tetrahydrofuran (10 ml) was then added dropwise, and the reaction stirred at room temperature for 18 hours. The mixture was evaporated under reduced pressure, the residue partitioned between dichloromethane and hydrochloric acid (2N) and the phases separated. The organic layer was washed with brine, dried (MgSO4) and evaporated under reduced pressure. The residue was triturated with diethyl ether, the resulting suspension filtered and the filtrate concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel using pentane:dichloromethane (75:25) as eluant to give the title compound, (2.0 g, 71%) as an oil.

Provenance & Evidence