Cesium carbonate → HCID 12164493, compound

Participants

Reaction Conditions

Reaction Steps

To dried trifluoro-p-cresol (531 mg, 3.27 mmol), copper(I) iodide (83 mg, 0.4 mmol), cesium carbonate (1.42 g, 4.36 mmol), 4-iodobenzonitrile (500 mg, 2.18 mmol) and N,N-dimethylglycine hydrochloride (91 mg, 0.65 mmol) under nitrogen was added degassed 1,4-dioxane (10.0 mL). The whole mixture was heated at 90° C. for 140 hours. The cooled mixture was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2×50 mL). The organic layers were combined and washed with brine (100 mL) and dried with Na2SO4 and concentrated in vacuo. The crude liquid was placed on a silica gel column and purified CH2Cl2/Hex (1:8→1:4) and then was recrystallized with hot hexane to give the product as white crystals (286 mg, 50%). 1H NMR (500 MHz, CDCL3) δ(ppm): 7.08 (1H, d, J=8.4 Hz), 7.15 (1H, d, J=8.8 Hz), 7.66 (1H, d, J=8.4 Hz), 7.67 (1H, d, J=8.8 Hz). 13C NMR (125 MHz, CDCL3) δ(ppm): 107.4, 118.7, 119.1 (CH), 120.0 (CH), 122.9, 125.1, 127.0 (1C, q, J=32.5 Hz), 127.3, 127.8 (2CH, q, J=3.8 Hz), 134.5 (CH), 158.2, 160.4. 19F (282 MHz, CDCL3) δ(ppm): −62.05 (3F, s). MS (FAB+): 264 (MH+). HRMS for C14H8F3NO (MH+): calculated: 264.0636; found 264.0621.

Provenance & Evidence