Hydrochloric Acid → 4-Propyl-1-(3-fluorophenyl)-cyclohexanol

3-Fluorobromobenzene (8) (10.0 g) and THF (100 ml) were put in a reaction vessel under a nitrogen atmosphere, and cooled to −74° C. n-Butyllithium (1.57 M, in a n-hexane solution; 40.0 ml) was added dropwise thereto in the temperature range of −74° C. to −70° C., and the mixture was stirred for another 2 hours. Subsequently, 4-propylhexanone (16) (12.0 g) in a THF (50 ml) solution was added dropwise thereto in the temperature range of −74° C. to −65° C., and the mixture was stirred for another 8 hours while allowing the temperature to come to 25° C. The reaction mixture obtained was poured into a vessel containing a 1N—HCl solution (500 ml) and ethyl acetate (300 ml), and mixed. The mixture was then allowed to stand until it had separated into organic and aqueous phases, and an extractive operation was carried out. The organic phase obtained was fractionated, washed with water, a saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate. Subsequently, the solvent was distilled off under reduced pressure, giving 13.5 g of 4-propyl-1-(3-fluorophenyl)-cyclohexanol (18). The compound (18) obtained was a yellow oil.

1. addition40.0 ml) was added dropwise
2. stirringin the temperature range of −74° C. to −65° C., and the mixture was stirred for another 8 hours
3. customto come to 25° C
4. customThe reaction mixture obtained
5. additionwas poured into a vessel
6. additionmixed
7. customhad separated into organic and aqueous phases
8. customThe organic phase obtained
9. washwashed with water
10. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate
11. distillationSubsequently, the solvent was distilled off under reduced pressure

ORD record

ord-ee04894301144576be7d39f7e348ee9f

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08187494B2