4-Chloroanisole → 1,1'-Biphenyl, 4,4'-dimethoxy-

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Reaktionsschritte

In the drybox, 20.0 mg (0.0876 mmol) of (Me2CH)PH(O)(2,4-(MeO)2C6H3) from Experiment 3, 20 mg (0.0218 mm) of Pd2(dba)3 and 5.0 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, 143.0 mg (1.0 mm) of 4-chloroanisole, 228 mg (1.5 mm) of 4-MeOC6H4B(OH)2 and 456 mg (3.0 mmol) of CsF were added into the reactor. The resulting mixture was refluxed for 60 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 213 mg (99% yield) of p-(4-methoxyphenyl)anisole. It was >95% pure by 1H NMR and GC/MS. 1H NMR (500 MHz, CDCl3): δ 7.38 (d, J=8.68 Hz, 4H), 6.86 (d, J=8.68 Hz, 4H), 3.74 (s, 6H) ppm. 13C NMR (125 MHz, CDCl3): δ 158.7, 133.5, 127.7, 114.2, 55.3 ppm. Anal Calcd for C14H14O2: C, 78.48; H, 6.59. Found: C, 78.44; H, 6.53.

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