Ethanol → Ethyl 3-bromo-5-(3-ethoxypropyl)-4-methylbenzoate

Participants

Reaction Steps

To an ethanol (0.1 M) solution of methyl 3-bromo-5-(3-iodopropyl)-4-methylbenzoate (1 eq.) from the previous step was added freshly prepared sodium ethoxide (3 eq.). The resulting solution was heated at reflux for 18 h. After cooling to RT, the volatiles were removed in vacuo. The resulting residue was then taken up in ether and washed further with 10% aq. HCl, 1 N aq. NaOH, water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product by way of flash chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc) afforded the title compound as a yellow oil.

Provenance & Evidence