تفاعل #60467

معادلة التفاعل

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

المردود 99.9%

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

المردود 99.9%

المذيبات

water

water

Ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   ترشيحwas filtered through Celite
2. 2
   استخلاصThe filtrate was then extracted with ethyl acetate
3. 3
   غسيلThe separated organic layer was washed with water and brine in that order
4. 4
   تجفيفdried over anhydrous magnesium sulfate
5. 5
   ترشيحThe desiccant was filtered off
6. 6
   تركيزthe filtrate was concentrated under reduced pressure
7. 7
   أخرىThe resultant residue was purified by NH silica gel column chromatography (hexane)

الإجراء التجريبي

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.

المصدر