تفاعل #315035

معادلة التفاعل

4-chloroacetophenone

3-methylphenylboronic acid

cesium fluoride

→

white solid

المردود 93.0%

3-methyl-4′-acetylbiphenyl

المردود 93.0%

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   أخرىAn oven dried resealable Schlenk tube
2. 2
   أخرىwas purged with argon
3. 3
   workup.ADDITIONwere added through a rubber septum
4. 4
   أخرىThe septum was removed
5. 5
   أخرىthe tube was sealed with a teflon
6. 6
   أخرىscrew cap
7. 7
   أخرىhad been completely consumed
8. 8
   workup.ADDITIONThe reaction mixture was then diluted with ether (20 mL)
9. 9
   workup.ADDITIONpoured into a separatory funnel
10. 10
    غسيلThe mixture was washed with 1M NaOH (20 mL)
11. 11
    أخرىthe layers were separated
12. 12
    استخلاصThe aqueous layer was extracted with ether (20 mL)
13. 13
    تجفيفthe combined organic extracts were dried over anhydrous magnesium sulfate
14. 14
    ترشيحfiltered
15. 15
    تركيزconcentrated in vacuo
16. 16
    أخرىThe crude material was then purified by flash chromatography on silica gel

الإجراء التجريبي

An oven dried resealable Schlenk tube was purged with argon and charged with palladium acetate (4.4 mg, 0.02 mmol, 2 mol %), ligand 2 [Example 1] (11.9 mg, 0.03 mmol, 3 mol %), 3-methylphenylboronic acid (204 mg, 1.5 mmol), and cesium fluoride (456 mg, 3.0 mmol). The tube was purged with argon, and dioxane (3 mL), and 4-chloroacetophenone (0.13 mL, 1.0 mmol) were added through a rubber septum. The septum was removed, the tube was sealed with a teflon screw cap and the mixture was stirred at room temperature until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (20 mL) and poured into a separatory funnel. The mixture was washed with 1M NaOH (20 mL), and the layers were separated. The aqueous layer was extracted with ether (20 mL), and the combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude material was then purified by flash chromatography on silica gel to give 195 mg (93%) of a white solid.

المصدر