Pyridine → (5-Bromopentyl)cyclohexane

To a stirred solution of 5-cyclohexylpentanol (1.74 g., 10.25 mmol) and pyridine (0.94 g., 11.1 mmol) at 0° under argon was added phosphorus tribromide (1.21 g., 4.5 mmol) dropwise. The reaction mixture became viscous, therefore 25 ml tetrahydrofuran was added. This mixture was stirred for 1.5 hours at room temperature, then partitioned between ethyl ether and 5% aqueous hydrochloric acid. The organic portion was washed with a 5% sodium bicarbonate solution, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give a dark yellow oil. Purification by flash chromatography (silica, hexane) yielded the desired alkyl halide.

1. custompartitioned between ethyl ether and 5% aqueous hydrochloric acid
2. washThe organic portion was washed with a 5% sodium bicarbonate solution, water, saturated sodium chloride solution
3. dry with materialdried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customto give a dark yellow oil
7. customPurification by flash chromatography (silica, hexane)

ORD record

ord-93b334b57cf84c8e8dca500a087d273c

Source dataset

uspto-grants-1992_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05134128