تفاعل #730155

معادلة التفاعل

4-chlorobiphenyl

(2-methylpropoxy)methyl boronic acid

2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl

cesium carbonate

→

title compound

المردود 28.5%

4-Isobutoxymethyl-biphenyl

المردود 28.5%

المذيبات

water

1,4-dioxane

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter the reaction mixture was cooled at room temperature
2. 2
   ترشيحfollowed by filtration
3. 3
   استخلاصAfter the filtrate was extracted with ethyl acetate
4. 4
   غسيلthe organic layer was washed with water
5. 5
   تجفيفan aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate
6. 6
   ترشيحfiltered
7. 7
   workup.DISTILLATIONThe solvent was distilled off from the filtrate under reduced pressure
8. 8
   أخرىThe residue was purified by silica gel column chromatography (heptane:ethylacetate=30:1)

الإجراء التجريبي

To a solution of 4-chlorobiphenyl (25 mg, 0.13 mmol) in 1,4-dioxane (1 ml) and water (100 μl) were added (2-methylpropoxy)methyl boronic acid (35 mg, 0.27 mmol), palladium (II) acetate (3.0 mg, 0.013 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (11 mg, 0.027 mmol), and cesium carbonate (130 mg, 0.40 mmol) at room temperature. The reaction mixture was stirred at 100° C. for 7 hours and 50 minutes under the nitrogen atmosphere. After the reaction mixture was cooled at room temperature, water was added to the mixture, followed by filtration using Celite. After the filtrate was extracted with ethyl acetate, the organic layer was washed with water and an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was distilled off from the filtrate under reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethylacetate=30:1) to obtain the title compound (9.0 mg, 0.037 mmol, 28%) as a colorless oil.

المصدر