تفاعل #60491

معادلة التفاعل

water

3-iodo-4-nitroanisole

4,4,5,5-tetramethyl-2-(3,3,5,5-tetramethylcyclohex-1-enyl)[1,3,2]dioxaborolane

tripotassium phosphate

water

→

title compound

المردود 34.3%

4-Methoxy-1-nitro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)benzene

المردود 34.3%

المذيبات

ethyl acetate

1,2-dimethoxyethane

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe mixture was then further stirred for 13 hours at an external temperature of 70° C
2. 2
   workup.STIRRINGby stirring for 26 hours at an external temperature of 100° C
3. 3
   درجة الحرارةThe reaction mixture was cooled
4. 4
   ترشيحthe mixture was filtered through Celite
5. 5
   تركيزThe filtrate was concentrated
6. 6
   أخرىto give a residue, which
7. 7
   استخلاصwas subjected to extraction with ethyl acetate
8. 8
   غسيلthe organic layer was washed with brine
9. 9
   تجفيفThe organic layer was dried over anhydrous magnesium sulfate
10. 10
    ترشيحthe desiccant was filtered off
11. 11
    تركيزthe filtrate was concentrated under reduced pressure
12. 12
    أخرىThe resultant residue was purified by silica gel column chromatography (ethyl acetate/heptane)

الإجراء التجريبي

To a solution of 3-iodo-4-nitroanisole (4.21 g, 15.1 mmol) in 1,2-dimethoxyethane (50 mL) were added 4,4,5,5-tetramethyl-2-(3,3,5,5-tetramethylcyclohex-1-enyl)[1,3,2]dioxaborolane (4.78 g, 18.1 mmol) produced in Example (4b), tripotassium phosphate (4.81 g, 22.7 mmol) and water (3 mL). Then, tetrakis(triphenylphosphine)palladium(0) (870 mg, 0.755 mmol) was added to the mixture while stirring at room temperature under a nitrogen atmosphere. The mixture was then further stirred for 13 hours at an external temperature of 70° C. To the reaction mixture were added tetrakis(triphenylphosphine)palladium(0) (870 mg, 0.755 mmol) and water (3 mL), followed by stirring for 26 hours at an external temperature of 100° C. The reaction mixture was cooled, and then ethyl acetate was added and the mixture was filtered through Celite. The filtrate was concentrated to give a residue, which was subjected to extraction with ethyl acetate, and the organic layer was washed with brine. The organic layer was dried over anhydrous magnesium sulfate and then the desiccant was filtered off and the filtrate was concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/heptane) to give 1.5 g of the title compound as a yellow solid.

المصدر