Chlorobenzene → Biphenyl

Participants

Reaction Steps

In the drybox, 14.4 mg (0.087 mmol) of (Me3C)2PH(O) from Experiment 2, 20.0 mg (0.0218 mmol) of Pd2(dba)3 and 4.0 mL of 1,4-dioxane were loaded into a reactor (20 mL) equipped with a magnetic stir bar. The resulting mixture was stirred at room temperature overnight. Next, 651 mg (2.0 mmol) of CsCO3 and 146.3 mg (1.2 mm) of PhB(OH)2 were added into the mixture above, followed by syringing 122 μl (1.2 mmol) of PhCl into the reactor. The resulting mixture was refluxed for 24 h. The reaction mixture was then cooled to room temperature, chromatographed on silicon gel using ethyl acetate/hexane (5% volume ratio) as eluant. The eluate was concentrated by rotary evaporation followed by high vacuum to yield 163 mg (88% yield) of biphenyl. It was >95% pure by 1H NMR and GC/MS. 1H NMR (500 MHz, CDCl3): δ 7.77 (d, J=7.75 Hz, 4H), 7.60 (t, J=7.65 Hz, 4H), 7.50 (t, J=7.38 Hz, 2H) ppm. 13C NMR (125 MHz, CDCl3): δ 141.2, 128.7, 127.2, 127.1 ppm.

Provenance & Evidence