Triphenylphosphine → Methyl [3-(3-bromopropoxy)phenyl]acetate

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 3-hydroxyphenylacetate (11.3 g, 0.068 mole) in 300 mL of anhydrous toluene was treated with 3-bromopropanol (12.2 g, 0.088 mole). Polymer bound triphenylphosphine (36.0 g, 0.108 mole, 3 mmol/g, Fluka Chemie) was then added, and the mixture reacted for 15 minutes. The reaction mixture was then cooled to 0° C. and diisopropylazodicarboxylate (16.9 g, 0.084 mol) was added in a dropwise fashion. After stirring at RT overnight, the crude reaction mixture was filtered and the solid washed with 100 mL toluene. After concentration of the filtrate in vacuo, the crude product was purified by column chromatography over silica gel (silica gel 60, EM Science) using 15% ethyl acetate:hexane as eluent to afford 15.8 g (81% yield) of the title compound as an oil: 1H NMR (CDCl3, 400 MHz) δ 7.23-7.19 (m, 1 H), 6.85-6.7 (m, 3), 4.09-4.06 (t, 2 H, J=5.8), 3.67 (s, 3 H), 3.67-3.56 (m, 4 H), 2.32-2.26 (p, 2 H, J=6.0); MS (ESI) 288 (MH+); TLC (hexanes:ethyl acetate/3:1) Rf=0.68. Anal. (C12H15O3Br) C, H, N.

Provenance & Evidence