Phosphorus tribromide → (3-Bromopropyl)cyclohexane

To the chilled (0° C.) 3-cyclohexyl-1-propanol (5 g, 35.15 mmol) was added slowly a solution of phosphorus tribromide (1.1 mL, 17.6 mmol) in dichloromethane (2 mL). Upon completion of the addition, the reaction mixture was allowed to warm up to room temperature and was stirred for 4 hours. The reaction was quenched by addition of saturated sodium bicarbonate aqueous solution (5 mL) and 10% NaOH (10 mL). The resulting mixture was extracted with diethyl ether (3×50 mL), the combined organic extracts were dried over sodium sulfate and the solvent was evaporated in vacuo to provide an oil. Vacuum distillation yielded 3.4 g (47% yield) of the title compound.

1. additionUpon completion of the addition
2. customThe reaction was quenched by addition of saturated sodium bicarbonate aqueous solution (5 mL) and 10% NaOH (10 mL)
3. extractionThe resulting mixture was extracted with diethyl ether (3×50 mL)
4. dry with materialthe combined organic extracts were dried over sodium sulfate
5. customthe solvent was evaporated in vacuo
6. customto provide an oil
7. distillationVacuum distillation

ORD record

ord-e4f97668bd144293b514783a795314a4

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08008342B2