Diphenylamine → HCID 22995277, compound

Participants

Reaction Conditions

Reaction Steps

A schlenk tube was charged with diphenylamine (0.97 g, 5.7 mmol), 4,4′-dibromobenzil (1.0 g, 2.7 mmol), Pd2(dba)3 (0.12 g, 0.13 mmol), dppf (0.15 g, 0.27 mmol), and NaOtBu (1.04 g, 11 mmol) in 50 mL of dry toluene. The reaction mixture was refluxed at 120° C. for 2 days under an argon atmosphere. The reaction mixture was then poured into a saturated NH4Cl aqueous solution and extracted with CH2Cl2. The combined organic layer was dried over anhydrous MgSO4 and the solvent was removed under reduced pressure. The product was purified by column chromatography (silica gel, dichloromethane:hexanes=2:1 (v/v)) to give a yellow solid (0.58 g, 39%). 1H NMR (300 MHz, CDCl3, δ): 7.67 (d, J=8.8 Hz, 4H), 7.07-7.33 (m, 20H), 7.01 (d, J=8.8 Hz). 13C{1H} NMR (75 MHz, CDCl3, δ): 193.82, 151.32, 146.62, 131.54, 130.50, 129.50, 125.72, 124.31, 119.87. IR (cm−1): 3059, 3055, 1646, 1636, 1585, 1489, 1311, 1278, 1172. Anal. Calcd for C38H28N2O2: C, 83.80; H, 5.18; N, 5.14. Found: C, 84.12; H, 5.44; N, 5.02.

Provenance & Evidence