Methanol → 4-Chloro-2-iodobenzeneethanol

Participants

Reaction Steps

A solution of 52.73 mmol of borane tetrahydrofuran complex (1N in tetrahydrofuran) is added dropwise to a stirred solution of 21.09 mmol of (4-chloro-2-iodo-phenyl)-acetic acid in 150 ml of dry tetrahydrofuran. The reaction mixture is stirred at room temperature for 1 hour then 20 ml of methanol are carefully added. The mixture is refluxed at 60° C. for 45 minutes, and then evaporated to dryness. The resulting residue is purified by flash chromatography (SiO2 60 F) to afford the title product as a yellowish solid. Rf=0.13 (EtOAc-heptane=1:4); Rt=4.27 (gradient I).

Provenance & Evidence