Benzene → (6-Bromohexyl)benzene

A solution of 6-bromohexanoyl chloride (49.7 g, 0.233 mol) in dry dichloromethane (40 ml) was added dropwise over 5 minutes to a suspension of aluminium chloride (31.0 g, 0.233 mol) in dry dichloromethane (100 ml), keeping the temperature between 20° C.-23° C. The mixture was stirred for 30 minutes at room temperature to give a yellow solution. Benzene (18.2 g, 0.233 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. This was then poured onto ice/water (200 g). A partial separation was achieved and the organic layer was washed with brine and water several times until the pH of the solution was neutral. The organic solution was dried (MgSO4) and evaporated under reduced pressure to a yellow oil. This was distilled under reduced pressure at 90° C.-110° C./0.5 mbar to give colourless oils. The relevant fractions were combined and purified by flash chromatography on silica gel using hexane to give 6-bromo-1-phenylhexane as a colourless oil (18.33 g, 33%).

1. custombetween 20° C.-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. additionThis was then poured onto ice/water (200 g)
7. customA partial separation
8. washthe organic layer was washed with brine and water several times until the pH of the solution
9. dry with materialThe organic solution was dried (MgSO4)
10. customevaporated under reduced pressure to a yellow oil
11. distillationThis was distilled under reduced pressure at 90° C.-110° C./0.5 mbar
12. customto give colourless oils
13. custompurified by flash chromatography on silica gel

ORD record

ord-4c88b9bb02df432d84d839d6805eb8c3

Source dataset

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05990102