Hydrogen Peroxide → 4'-METHOXY-2-NITROBIPHENYL

Participants

Reaction Steps

A solution of 4-methoxyphenylboronic acid (11.0 g, 72 mmol) in 95% EtOH (100 mL) was added to a solution of (Ph3P)4Pd (2.25 g, 2.0 mmol) and 1-bromo-2-nitrobenzene (13.0 g, 65 mmol) in benzene (300 mL). A solution of Na2CO3 (2M, 150 mL, 300 mmol) was added, and the resulting mixture was refluxed with vigorous stirring overnight. The reaction mixture was then cooled, 30% H2O2 (20 mL) was added, and stirring was continued for 1 h. The resulting mixture was extracted with Et2O, the organic extract was rinsed with brine, dried (Na2SO4), and the solvent was removed in vacuo. The residue was taken up in CH2Cl2 :hexane 1:3, filtered through silica gel, and the biphenyl was eluted with CH2Cl2 :Hexane 1:1. The solvent was removed in vacuo to afford a yellow solid (15.5 g, quantitative yield): mp 48°-50° C.; [Jones, B.; Chapman, F., J. Chem. Soc. 1829-1832 (1952)]1H NMR (CDCl3) δ7.78 (d, 1H, J=8.4 Hz), 7.57 (t, 1H, J=7.8 Hz), 7.42 (m, 2H), 7.24 (d, 2H, J=9.0 Hz 6.94 (d, 2H, J=9.0 Hz), 3.83 (s, 3H); 13C NMR (CDCl3) δ159.70, 149.42, 135.85, 132.13, 131.92, 129.49, 129.12, 127.72, 123.99, 114.22, 55.31. Anal. Calcd for C13H11NO3 : C, 68.11; H, 4.84; N, 6.11. Found: C, 68.42; H, 4.79; N, 5.83.

Provenance & Evidence