تفاعل #730150

معادلة التفاعل

water

heptane

4-chlorobiphenyl

1,4-dioxane

water

cesium carbonate

→

title compound

المردود 90.0%

4-Cyclopropylmethoxymethyl-biphenyl

المردود 90.0%

ظروف التفاعل

المعالجة

1. 1
   أخرى30 minutes
2. 2
   درجة الحرارةAfter the reaction mixture was cooled at room temperature
3. 3
   ترشيحfollowed by filtration
4. 4
   غسيلThe separated organic layer was washed with an aqueous saturated sodium chloride solution
5. 5
   أخرىThe organic layer was separated
6. 6
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
7. 7
   أخرىThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=30:1)

الإجراء التجريبي

To a mixture of 4-chlorobiphenyl (50 mg, 265 μmol) and 1,4-dioxane (2 ml) were added water (0.2 ml), cesium carbonate (259 mg, 795 μmol), potassium cyclopropylmethoxymethyl trifluoroborate (102 mg, 530 mol), palladium (II) acetate (5.95 mg, 27 μmol) and 2-dicycrohexylphospino-2′,6′-dimethoxybiphenyl (21.8 mg, 53.1 μmol). Then, the reaction mixture was stirred at 100° C. (external temperature) for 7 hours and 30 minutes. After the reaction mixture was cooled at room temperature, water and heptane were added to the mixture, followed by filtration using Celite. The separated organic layer was washed with an aqueous saturated sodium chloride solution. The organic layer was separated, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=30:1) to obtain the title compound (57 mg, 239 μmol, 90%).

المصدر