Reaktion #315035

Reaktionsgleichung

4-chloroacetophenone

3-methylphenylboronic acid

cesium fluoride

→

white solid

Ausbeute 93.0%

3-methyl-4′-acetylbiphenyl

Ausbeute 93.0%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAn oven dried resealable Schlenk tube
2. 2
   Sonstigewas purged with argon
3. 3
   workup.ADDITIONwere added through a rubber septum
4. 4
   SonstigeThe septum was removed
5. 5
   Sonstigethe tube was sealed with a teflon
6. 6
   Sonstigescrew cap
7. 7
   Sonstigehad 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
    WaschenThe mixture was washed with 1M NaOH (20 mL)
11. 11
    Sonstigethe layers were separated
12. 12
    ExtraktionThe aqueous layer was extracted with ether (20 mL)
13. 13
    Trocknenthe combined organic extracts were dried over anhydrous magnesium sulfate
14. 14
    Filtrationfiltered
15. 15
    Einengenconcentrated in vacuo
16. 16
    SonstigeThe crude material was then purified by flash chromatography on silica gel

Vorschrift

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.

Quelle