1-(2-BROMOETHOXY)-4-TERT-BUTYLBENZENE synthesis

Yield:5952-59-0 62%

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