Water → 3-Methoxybiphenyl

The procedure from Example above was followed using 110 mg (0.609 mmol) of (Me3C)2P—Cl, 67 mg (0.299 mmol) of Pd(OAc)2, 60 mg (3.3 mmol) of H2O, and 3-chloroanisole (1.43 g, 10.0 mm), C6H5B(OH)2 (1.83 g, 15.0 mm) and CsF (4.56 mg, 30.0 mmol) in 15 mL of 1,4-dioxane. After the mixture was refluxed for 42 h, the reaction mixture was then cooled to room temperature, quenched with 50 mL of H2O, and extracted with 300 mL of diethyl ether. The organic extracts were washed with H2O (2×50 mL), brine (50 mL), and dried over mgSO4, filtered, and the ether and dioxane removed from the filtrate by rotary evaporation. The resulting residue was chromatographed on silicon gel using hexane as eluant. The eluate was concentrated by rotary evaporation followed by high vacuum to give 1.49 g (81% yield) of 3-phenylanisole. It was >95% pure by 1H NMR and GC/MS.

1. temperatureAfter the mixture was refluxed for 42 h
2. customquenched with 50 mL of H2O
3. extractionextracted with 300 mL of diethyl ether
4. washThe organic extracts were washed with H2O (2×50 mL), brine (50 mL)
5. customdried over mgSO4
6. filtrationfiltered
7. customthe ether and dioxane removed from the filtrate by rotary evaporation
8. customThe resulting residue was chromatographed on silicon gel
9. concentrationThe eluate was concentrated by rotary evaporation

ORD record

ord-ea9a6f31ddf94ddda2a81df9fbf9ad77

Source dataset

uspto-grants-2004_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06762330B2