1-(3-BROMOPROPOXY)-3-METHYLBENZENE synthesis
- Product Name:1-(3-BROMOPROPOXY)-3-METHYLBENZENE
- CAS Number:6291-74-3
- Molecular formula:C10H13BrO
- Molecular Weight:229.11
Yield:6291-74-3 75%
Reaction Conditions:
with potassium carbonate in acetonitrile;Reflux;
Steps:
General procedure for the side chain (7a-7m)
General procedure: To a suspension of phenol(or thiophenol) (60 mmol, 1 eq.) and K2CO3 powder (24.8 g, 180 mmol, 3 eq.) in acetonitrile (100 mL) with stirring was added 1,3-dibromopropane (18.5 mL,180 mmol, 3 eq.) or 1,2-dibromoethane (12.6 mL,180 mmol, 3 eq.) at room temperature. The reaction mixture was refluxed for 3h -12 h, and monitored by TLC till the phenol was disappeared. After the reaction, the K2CO3 was removed by filtration and solvent was removed under reduced pressure to give the crude product which was then purified by column chromatography using ethyl acetate: petroleum ether(1:50-1:20). The products (7a-7m) were obtained as colorless to yellow oils with yields of 60% to 93%.
References:
Luan, Shenglin;Ge, Qi;Chen, Yedong;Dai, Mingyang;Yang, Jinyu;Li, Kun;Liu, Dan;Zhao, Linxiang [Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,# 9,p. 1943 - 1948] Location in patent:supporting information