Réaction #60491

Équation de réaction

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

Rendement 34.3%

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

Rendement 34.3%

Solvants

ethyl acetate

1,2-dimethoxyethane

Conditions de réaction

Traitement

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
   TempératureThe reaction mixture was cooled
4. 4
   Filtrationthe mixture was filtered through Celite
5. 5
   ConcentrationThe filtrate was concentrated
6. 6
   Autreto give a residue, which
7. 7
   Extractionwas subjected to extraction with ethyl acetate
8. 8
   Lavagethe organic layer was washed with brine
9. 9
   SéchageThe organic layer was dried over anhydrous magnesium sulfate
10. 10
    Filtrationthe desiccant was filtered off
11. 11
    Concentrationthe filtrate was concentrated under reduced pressure
12. 12
    AutreThe resultant residue was purified by silica gel column chromatography (ethyl acetate/heptane)

Mode opératoire

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.

Source