1-Chloro-2-nitrobenzene → 2-Nitrobiphenyl

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Reaction Steps

According to General Procedure A, a mixture of o-chloronitrobenzene (79 mg, 0.50 mmol), phenylboronic acid (91 mg, 0.75 mmol), CsF (228 mg, 1.50 mmol), Pd(OAc)2 (2 mg, 0.01 mmol) and 12f (8 mg, 0.02 mmol) in 1,4-dioxane (2.5 mL) has heated to reflux, cooled and filtered. Evaporation of the solvent under reduced pressure and column chromatography of the pre-adsorbed crude material (1% Et2O in hexane, silica gel) gave 51d (73 mg, 73%) as a bright yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.86 (d, 1H, J=8.0 Hz), 7.62 (t, 1H, J=7.5 Hz), 7.51-7.40 (m, 5H), 7.34-7.31 (m, 2H); 13C NMR (75.5 MHz, CDCl3) δ 149.3, 137.4, 136.3, 132.2, 131.9, 128.7, 128.2, 128.1, 127.9, 124.0.

Provenance & Evidence