Reaktion #1276784

Reaktionsgleichung

ethanol

sodium carbonate

1-bromo-2-methoxynaphthalene

2-fluorophenylboronic acid

→

1-(2-Fluorophenyl)-2-methoxynaphthalene

Ausbeute 60.0%

Lösungsmittel

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a 500 mL three-neck flask were placed
2. 2
   Sonstigeto be degassed
3. 3
   workup.STIRRINGthe mixture was stirred at 80° C. for 8 hours under a nitrogen stream
4. 4
   ExtraktionThe aqueous layer of the obtained mixture was subjected to extraction with toluene
5. 5
   Extraktionthe obtained solution of the extract
6. 6
   Waschenwashed with saturated brine
7. 7
   TrocknenThe organic layer was dried with magnesium sulfate
8. 8
   Filtrationthis mixture was gravity-filtered
9. 9
   SonstigeAn oily substance obtained by concentration of the obtained filtrate
10. 10
    FiltrationThis solution was suction-filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135)
11. 11
    SonstigeAn oily substance obtained by concentration of the obtained filtrate
12. 12
    Sonstigewas dried under reduced pressure, so that 5.3 g of a pale yellow oily substance of the object of the synthesis
13. 13
    Sonstigewas obtained in 60% yield
14. 14
    SonstigeThe reaction scheme of Step 1

Vorschrift

Into a 500 mL three-neck flask were placed 8.7 g (35 mmol) of 1-bromo-2-methoxynaphthalene, and 5.0 g (35 mmol) of 2-fluorophenylboronic acid. The air in the flask was replaced with nitrogen. To this mixture were added 120 mL of toluene, 60 mL of ethanol, and 40 mL of an aqueous solution of sodium carbonate (2.0 mol/L). While the pressure was reduced, this mixture was stirred to be degassed. To this mixture was added 2.0 g (1.7 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at 80° C. for 8 hours under a nitrogen stream. The aqueous layer of the obtained mixture was subjected to extraction with toluene, and the obtained solution of the extract and the organic layer were combined and washed with saturated brine. The organic layer was dried with magnesium sulfate, and this mixture was gravity-filtered. An oily substance obtained by concentration of the obtained filtrate was dissolved in about 30 mL of toluene. This solution was suction-filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). An oily substance obtained by concentration of the obtained filtrate was dried under reduced pressure, so that 5.3 g of a pale yellow oily substance of the object of the synthesis was obtained in 60% yield. The reaction scheme of Step 1 is illustrated in (E2-1).

Quelle