Potassium Iodide → HCID 22709078, Verbindung

Temperatur

80 °C

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.

1. temperatureThe reaction mixture was cooled
2. extractionextracted with 2×500 ml of ethyl acetate
3. washThe combined organic extracts were washed with saturated NaCl solution (3×100 ml)
4. dry with materialdried over magnesium sulfate
5. customevaporated to dryness
6. dissolutionThis 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
7. temperatureThe resulting solution was cooled to 5° C
8. additionA solution of bis-trimethylsilyl sulfate (0.38 g) in 10 ml of dichloromethane was then added dropwise to the reaction mixture
9. stirringThe resulting mixture was stirred for two hours at 5° C
10. additionTriethylamine (4 ml) was added to the reaction mixture
11. stirringstirring
12. waitwas continued for one hour at room temperature
13. additionThe reaction mixture was then poured into 300 ml of water
14. extractionextracted with dichloromethane (2×300 ml)
15. dry with materialThe combined organic extracts were dried over magnesium sulfate
16. customevaporated to dryness
17. customto give 33.95 g of a slightly beige residue, which
18. filtrationwas then filtered through a silica gel column

ORD-Eintrag

ord-fda3bf01cd6840e18b5c43b4bb7e28f8

Quelldatensatz

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06746729B1