Anisole → Benzene, 1-(6-bromohexyl)-4-methoxy-

A solution of 6-bromohexanoyl chloride (50 g, 0.2 mol) in dry dichloromethane (40 ml) was added dropwise over 5 minutes to a suspension of aluminium chloride (31 g, 0.2 mol) in dry dichloromethane (100 ml), keeping the temperature between 20-23° C. The mixture was stirred for 30 minutes at room temperature to give a yellow solution. Anisole (23 g, 0.2 mol) in dry dichloromethane (30 ml) was added and stirred for 20 hours at room temperature. Triethylsilane (59.9 g, 0.515 mol) was added over 10 minutes, maintaining the temperature between 25° C.-35° C. The solution was stirred for 60 minutes at room temperature and poured onto ice/water (200 g). The organic layer was washed with brine and water until the pH of the solution was neutral. Drying (MgSO4) and evaporation under reduced pressure gave a yellow oil which was distilled under reduced pressure at 90-110° C./0.5 mbar. Produce containing fractions were combined and purified by flash chromatography on silica gel using hexane as eluant to give a colourless oil (18.33 g, 33%).

1. custombetween 20-23° C
2. customto give a yellow solution
3. stirringstirred for 20 hours at room temperature
4. temperaturemaintaining the temperature between 25° C.-35° C
5. stirringThe solution was stirred for 60 minutes at room temperature
6. additionpoured onto ice/water (200 g)
7. washThe organic layer was washed with brine and water until the pH of the solution
8. customDrying
9. custom(MgSO4) and evaporation under reduced pressure
10. customgave a yellow oil which
11. distillationwas distilled under reduced pressure at 90-110° C./0.5 mbar
12. customProduce
13. additioncontaining fractions
14. custompurified by flash chromatography on silica gel

ORD record

ord-ce3f834a661748b7bcee41cc14f43abe

Source dataset

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05990102