Water → 4-Methoxybiphenyl

To a rubber-capped Schlenk vessel was added K3PO4 (298.4 mg, 1.4 mmol). This equipment was dried with flame under vacuum and backfilled with nitrogen for three times. Then Pd(OAc) (2.7 mg, 0.012 mmol), dicyclohexyl(2,4,6-trimethoxyphenyl)phosphine tetrafluoroborate (11.0 mg, 0.024 mmol), phenyl bronic acid (99.8 mg, 98%, 0.80 mmol), and 0.5 mL of dioxane were added sequentially to the Schlenk vessel. After being stirred for about 5 min at room temperature, p-methoxyphenyl chloride (56.5 mg, 0.40 mmol), another 0.5 mL of dioxane, and 21.5 μL of water (21.5 mg, 1.2 mmol) were added sequentially in one portion. The resulting mixture was heated at 110° C. with a preheated oil bath. After 11 h, the reaction was complete as monitored by GC. The reaction mixture was then cooled and diluted by 10 mL of CH2Cl2 and filtered through a short column of silica gel (eluent: 2×10 mL of CH2Cl2). Evaporation and purification by chromatography (petroleum ether/ether=60/1) on silica gel afforded 4-Methoxybiphenyl (65.9 mg, 90%)

1. customThis equipment was dried
2. temperaturewith flame under vacuum
3. temperatureThe resulting mixture was heated at 110° C. with a preheated oil bath
4. waitAfter 11 h
5. temperatureThe reaction mixture was then cooled
6. filtrationfiltered through a short column of silica gel (eluent: 2×10 mL of CH2Cl2)
7. customEvaporation and purification by chromatography (petroleum ether/ether=60/1) on silica gel

ORD record

ord-79ff9245706149588ee5349fdaf64a44

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09006491B2