반응 #60467

반응 방정식

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

수율 99.9%

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

수율 99.9%

용매

water

water

Ethyl acetate

반응 조건

후처리

1. 1
   여과was filtered through Celite
2. 2
   추출The filtrate was then extracted with ethyl acetate
3. 3
   세척The separated organic layer was washed with water and brine in that order
4. 4
   건조dried over anhydrous magnesium sulfate
5. 5
   여과The desiccant was filtered off
6. 6
   농축the filtrate was concentrated under reduced pressure
7. 7
   기타The resultant residue was purified by NH silica gel column chromatography (hexane)

실험 절차

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.

출처