Cyclohexyl bromide → HCID 66925034, compound

Temperature

50 °C

Under an argon atmosphere, to a solution of ethyl 1H-pyrrole-3-carboxylate (2.09 g) and aluminum(III) chloride (4.0 g) in carbon disulfide (30 mL) was added bromocyclohexane (1.84 mL) under ice-cooling with stirring, and the mixture was stirred at room temperature for 30 min. The mixture was heated to 50° C., and stirred for 2 hr. The reaction product was cooled to room temperature, poured into ice water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→8:2), and recrystallized from hexane to give the title compound as a colorless solid (yield 530 mg, 16%).

1. temperaturecooling
2. stirringthe mixture was stirred at room temperature for 30 min
3. stirringstirred for 2 hr
4. temperatureThe reaction product was cooled to room temperature
5. extractionthe mixture was extracted with ethyl acetate
6. washThe extract was washed with saturated brine
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→8:2)
10. customrecrystallized from hexane

ORD record

ord-62cee19ab8e14936ba829df650d901c8

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08048909B2