Bromocyclopentane → HCID 19384666, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence