Potassium Iodide → HCID 22709078, compound

Participants

Reaction Conditions

Reaction Steps

A mixture consisting of 4-bromophenol (20.75 g), 6-chloro-1-hexanol (20.50 g), potassium carbonate (33.20 g) and potassium iodide (21.9 g) in dimethylsulfoxide was stirred for 6 hours at 80° C. The reaction mixture was cooled and poured into 500 ml of water and extracted with 2×500 ml of ethyl acetate. The combined organic extracts were washed with saturated NaCl solution (3×100 ml) dried over magnesium sulfate and evaporated to dryness. This gave 37.4 g of a slightly beige oil of which 24.9 g were dissolved in 250 ml of dichloromethane containing 8.05 g of 3.4-didydro-2H-pyran. The resulting solution was cooled to 5° C. A solution of bis-trimethylsilyl sulfate (0.38 g) in 10 ml of dichloromethane was then added dropwise to the reaction mixture. The resulting mixture was stirred for two hours at 5° C. Triethylamine (4 ml) was added to the reaction mixture and stirring was continued for one hour at room temperature. The reaction mixture was then poured into 300 ml of water and extracted with dichloromethane (2×300 ml). The combined organic extracts were dried over magnesium sulfate and evaporated to dryness to give 33.95 g of a slightly beige residue, which was then filtered through a silica gel column using a cyclohexane/ethyl acetate (8/2) as eluent to give 28.9 g of 4-bromo-1-[6-(tetrahydropyran-2-yloxy)hexyloxy]benzene as colourless oil.

Provenance & Evidence