1,5-Dibromopentane → (5-Bromopentyl)cyclohexane

Temperature

0 °C

To a solution of 1,5-dibromopentane (16 gm, 69.97 mmol) in THF (20 ml) was added a solution of (Li2CuCl4 in ether, 14 ml) under nitrogen at 5-10° C. and stirred for 25 minutes. Cyclohexyl magnesium bromide (10 gm, 69.97 mmol) was added dropwise with stirring for about 30 minutes. The reaction mixture was stirred at 0° C. for another 1 h and stirred at room temperature for 12 hr. The reaction mixture was cooled to 0° C. in ice, saturated NH4Cl solution (20 ml) was added and the resulting mixture was extracted with EtOAc (4×25 ml). The organic layer was separated, washed with brine and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by column chromatography using hexane as an eluent. The pure product was an oily liquid (12.84 gm).

1. stirringwith stirring for about 30 minutes
2. stirringThe reaction mixture was stirred at 0° C. for another 1 h
3. stirringstirred at room temperature for 12 hr
4. extractionthe resulting mixture was extracted with EtOAc (4×25 ml)
5. customThe organic layer was separated
6. washwashed with brine
7. dry with materialdried over anhydrous Na2SO4
8. customThe solvent was removed under reduced pressure
9. customthe crude product was purified by column chromatography

ORD record

ord-21aa28c1aefa4197a806790588328b18

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08288410B2