Bromocyclopentane → HCID 19384666, compound

Temperature

100 °C

4-Fluorophenylacetonitrile (10 g, 74 mmol) was combined with tetrabutylammonium bromide (2.76 g), 50% sodium hydroxide (38 g), and sodium hydroxide pellets (8.5 g, 213 mmol). The flask was warmed to 50° C. (internal) and bromocyclopentane (8.57 mL, 80 mmol) was added over a 5 minute period. The temperature was raised to 100° C. and maintained for 30 minutes. Workup consisted of pouring the reaction mixture onto ice (100 mL) and extracting with ether (100 mL, then 2×50 mL). The combined ethereal extracts were washed with saturated with sodium chloride solution (20 mL), dried using MgSO4, filtered through silica, and concentrated. The residue was subjected to vacuum distillation, affording the a product compound as an oil, which was characterized as follows: 13CNMR(CDCl3, 100 MHz, partial): 45.3, 41.7, 30.9, 30.2, 24.9, 24.8. NMR(CDCl3, 400 MHz, partial): 3.72(d, 1H, J=7 Hz).

1. additionwas added over a 5 minute period
2. temperaturemaintained for 30 minutes
3. additionof pouring the reaction mixture onto ice (100 mL)
4. extractionextracting with ether (100 mL
5. washThe combined ethereal extracts were washed with saturated with sodium chloride solution (20 mL)
6. customdried
7. filtrationfiltered through silica
8. concentrationconcentrated
9. distillationThe residue was subjected to vacuum distillation
10. customaffording the a product compound as an oil, which

ORD record

ord-818d3c13032e453ead81e71b640ad59a

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06265439B1