Réaction #60467

Équation de réaction

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

2-bromo-3-nitrotoluene

tripotassium phosphate

1,2-dimethoxyethane

→

title compound

Rendement 99.9%

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

Rendement 99.9%

Solvants

water

water

Ethyl acetate

Conditions de réaction

Traitement

1. 1
   Filtrationwas filtered through Celite
2. 2
   ExtractionThe filtrate was then extracted with ethyl acetate
3. 3
   LavageThe separated organic layer was washed with water and brine in that order
4. 4
   Séchagedried over anhydrous magnesium sulfate
5. 5
   FiltrationThe desiccant was filtered off
6. 6
   Concentrationthe filtrate was concentrated under reduced pressure
7. 7
   AutreThe resultant residue was purified by NH silica gel column chromatography (hexane)

Mode opératoire

A mixture of 4,4,5,5-tetramethyl-2-(3,3,5,5-tetramethylcyclohex-1-enyl)[1,3,2]dioxaborolane (3.96 g, 15 mmol) produced in Example (4b), 2-bromo-3-nitrotoluene (2.48 g, 11.5 mmol), tetrakis(triphenylphosphine)palladium(0) (1.33 g, 1.15 mmol), tripotassium phosphate (3.66 g, 17.3 mmol), 1,2-dimethoxyethane (30 mL) and water (10 mL) was stirred for 10 hours and 20 minutes at an external temperature of 80° C. under a nitrogen atmosphere. Ethyl acetate and water were added to the reaction mixture, and it was filtered through Celite. The filtrate was then extracted with ethyl acetate. The separated organic layer was washed with water and brine in that order and then dried over anhydrous magnesium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The resultant residue was purified by NH silica gel column chromatography (hexane) to give 3.14 g of the title compound as a yellow oil.

Source