Water → 1-(4-Bromophenyl)cyclobutanecarbonitrile

Participants

Reaction Conditions

Reaction Steps

KOH (11.4 g, 204 mmol, 8 eq), water (3.75 mL), 4-bromophenylacetonitrile (5.00 g, 25.5 mmol, 1.0 eq), 1,3-dibromopropane (5.15 g, 25.5 mmol, 1.0 eq), tetrabutylammonium bromide (82 mg, 0.26 mmol, 0.01 eq), and toluene (68 mL) were slowly stirred while heating to 100° C. The biphasic reaction was kept at 100° C. for 30 minutes. The heat was removed, the reaction was slightly cooled, the stirring was then increased to rapid, and then heating continued up to reflux, 115° C. After 1.5 hours at 115° C., the reaction was cooled, diluted with water, and extracted with EtOAc (×3). The combined organics were dried with brine and Na2SO4, and then concentrated in vacuo onto Celite. The resulting material was purified by silica gel chromatography by eluting with a gradient of heptane and EtOAc (0% to 35% EtOAc) to provide Compound [CXXXIV]: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.99-2.15 (m, J=11.52, 9.02, 9.02, 4.40, 4.40 Hz, 1H) 2.34-2.51 (m, 1H) 2.51-2.65 (m, 2H) 2.74-2.89 (m, 2H) 7.21-7.36 (m, 2H) 7.45-7.57 (m, 2H).

Provenance & Evidence