4-Iodobenzonitrile → HCID 57390371, compound

Participants

Reaction Conditions

Reaction Steps

Potassium tert-butoxide (1.0 M in THF, 10.5 mL) was slowly added to a solution of 4-hydroxypyridine (997 mg, 10.5 mmol) in anhydrous DMSO (10.0 mL). After the mixture was stirred for 3 hours, a solution of 4-iodobenzonitrile (1.2 g, 5.2 mmol) in DMSO (10.0 mL) was added and the reaction mixture was heated at 160° C. for 44 hours. The mixture was cooled to room temperature and partitioned between methylene chloride (100 mL) and water (100 mL). The organic layer was separated and the aqueous layer was extracted with methylene chloride (2×100 mL). The organic layers were combined and concentrated in vacuo. The crude solid was purified by silica gel column chromatography (Hex/EtOAc 1:1) then (CH2Cl2/MeOH 98:2 to 96:4) to give the product as a light yellow solid (480 mg, 47%). 1H NMR (500 MHz, CDCL3) δ(ppm): 6.52 (2H, d, J=8.0 Hz), 7.53 (2H, d, J=8.8 Hz), 7.64 (2H, d, J=8.0 Hz), 7.87 (2H, d, J=8.8 Hz). 13C NMR (125 MHz, CDCL3) δ(ppm): 112.4, 117.6, 119.8 (CH), 123.2 (CH), 134.5 (CH), 138.2 (CH), 146.2, 179.0. MS (FAB+): 197 (MH+). HRMS for O12H8N2O (MH+): calculated: 197.0715; found 197.0716.

Provenance & Evidence