Methanol → 4-Chloro-2-iodobenzeneethanol

Reaction equation

O1CCCC1.B.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15](O)=[O:16])=[C:10]([I:18])[CH:9]=1.CO>O1CCCC1>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[C:10]([I:18])[CH:9]=1

Participants

Procedure

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).