HCID 10785365, compound → 4,4′-Dinitro[1,1′-biphenyl]-2-carbonitrile

Participants

Reaction Steps

A solution of the iodide 77 (5.0 g, 13.66 mmol) and CuCN (1.65 g, 18.42 mmol) in 30 mL of anhydrous dimethiylsulfoxide was heated (180° C.) under an argon atmosphere. After 2 hr, the reaction mixture was added to a 0° solution of aqueous ammonium chloride (100 mL) and filtered through a Buchner funnel. The insoluble product was partitioned into methylene chloride and water. The separated or ganic layer was dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography (1/1 Hexane/CH2Cl2 to 30%/69%/1% Hexane(CH2Cl2 /MeOH) to afford the nitrile 78 (3.3 g, 12.27 mmol, 90% from 77) as a light yellow solid. 1H NMR (DMSO-d6) δ8.69 (d, 1H, J=2.3), 8.56 (dd, 1H, J1 =8.6, J=2.3), 8.44-8.41 (m, 2H), 7.80-7.76 (m, 3H).

Provenance & Evidence