tert-Butyl Hydroperoxide (70% in Water)

Used Chemicals

• Benzylamine [B0406]
• tert-Butyl Hydroperoxide (70% in Water) (= TBHP) [B3153]
• Cesium Carbonate [C2160]
• Acetonitrile

Procedure

To a solution of benzylamine (107 mg, 1.0 mmol) and cesium carbonate (326 mg, 3.0 mmol, 3.0 eq.) in acetonitrile (5 mL) was added TBHP (0.41 mL, 3.0 mmol, 3.0 eq.) at r.t. and the mixture was stirred at 80 °C for 17 hours. The reaction mixture was directly purified by column chromatography (on silica gel, ethyl acetate:hexane = 0:1 - 1:1) to give benzamide as a white solid (63 mg, 52% yield).

Experimenter’s Comments

The reaction mixture was monitored by UPLC.

Analytical Data

benzamide

¹H NMR (270 MHz, CDCl₃); δ 7.96 (m, 1H), 7.87 (d, 2H, J = 7.0 Hz), 7.54-7.28 (m, 4H).

Lead Reference

• Base promoted peroxide systems for the efficient synthesis of nitroarenes and benzamides
  • S. Gupta, A. Ansari, K. V. Sashidhara, Tetrahedron Lett. 2019, 60, 151076.

References

• X. Li, X. Shi, M. Fang, X. Xu, J. Org. Chem. 2013, 78, 9499.