1,6-Dibromohexane → 1-(4-((6-Bromohexyl)oxy)butyl)-4-nitrobenzene

A stirred mixture of 4-(4-nitrophenyl)butan-1-ol (2.0 g, 10 mmol), tetra-n-butylammomium hydrogen sulfate (0.17 g, 0.5 mmol), and 1,6-dibromohexane (3.2 mL, 20 mmol) in dichloromethane (10 mL) was treated with aqueous sodium hydroxide solution (10 M, 1 mL). The reaction mixture was stirred for 6 days at room temperature. The organic and aqueous phases were separated. The aqueous phase was extracted thrice with dichloromethane. The combined organics were washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified via automated flash silica gel chromatography, using a 40 g Silicycle SiliSep flash column (hexanes/ethyl acetate). Concentration of the desired fractions under reduced pressure provided the title compound as pale straw-colored oil (0.72 g, 20%). ES/MS calcd. for C16H25BrNO3+ 358.1. Found m/z=358.2 (M+H)+.

1. customThe organic and aqueous phases were separated
2. extractionThe aqueous phase was extracted thrice with dichloromethane
3. washThe combined organics were washed with water
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe crude residue was purified via automated flash silica gel chromatography

ORD record

ord-f2482060751d47a482f64d99a680b4c7

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394829B2