1,3-Dibromopropane → 1-[4-(3-Bromopropoxy)-3-methoxyphenyl] phenylmethanone

Participants

Reaction Steps

A mixture of 1-(4-hydroxy-3-methoxyphenyl)phenylmethanone (14 g, 61.4 mmol), K2CO3 (13 g, 92.1 mmol), and 1.3-dibromopropane (28 g, 86 mmol) in acetonitrile (400 ml) was heated at reflux for 4 hours. The reaction was followed by thin layer chromatography. At the end of the reaction, the inorganics were filtered off and the solvent was removed on a rotary evaporator. The residue was purified on a flash chromatographic column (SiO2, 140 g, eluted with 4:1 hexane:dichloromethane, 1.2 l) to give a partially solidified material; 15.44 g (72%). Recrystallization twice from ethanol gave 2.84 g of 1-[4-(3-bromopropoxy)-3-methoxylphenyl]phenylmethanone as white crystals, m.p.=88°-89° C. ANALYSIS: Calculated for C12H17BrO3: 58.47%C 4.91%H 5.19%N Found: 59.03%C 4.87%H

Provenance & Evidence