1-Iodo-3-(phenethoxymethyl)benzene synthesis

Yield:1222138-98-8 99%

Reaction Conditions:

Stage #1: 2-phenylethanolwith sodium hydride in tetrahydrofuran at 25;Cooling with ice;
Stage #2: m-Iodobenzyl bromidewith tetrabutylammomium bromide in tetrahydrofuran at 25; for 20 h;

Steps:

28

Into a 100 mL round-bottom flask was placed under N₂ a solution of 2- phenylethanol (110 mg, 0.90 mmol) in tetrahydrofuran (10 mL). Sodium hydride (26 mg, 1.08 mmol, 1.2 equiv.) was added with ice cooling. The mixture was stirred for 2 h at 25 ⁰C, then 3-iodobenzyl bromide (320 mg, 1.08 mmol, 1.2 equiv.) and W-Bu₄NBr (30 mg, 0.09 mmol, 0.10 equiv.) were added. The resulting solution was stirred for 20 h at 25 ⁰C. The reaction progress was monitored by TLC (SiO₂, EtO Ac/petroleum ether 1:5). The reaction was quenched by the addition of saturated aqueous NH₄Cl solution. The resulting solution was extracted with EtOAc, and the organic layers were combined, dried over Na₂SO₄, and concentrated under vacuum. The residue was chromato graphed on silica gel with EtOAc/petroleum ether 1:20 to obtain 300 mg (99%) of l-iodo-3- (phenethoxymethyl)benzene as a yellow oil.

References:

WO2010/45212,2010,A2 Location in patent:Page/Page column 247-248