Reaktion #80924

Reaktionsgleichung

sodium methoxide

4-chlorophenol

1,3-dibromobenzene

→

3-(4-chlorophenoxy)phenyl bromide

Ausbeute 29.9%

Lösungsmittel

diglyme

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONUpon completion of addition
2. 2
   Sonstigeto remove methanol
3. 3
   SonstigeAfter the methanol was removed
4. 4
   TemperaturUpon completion of the additions, the reaction mixture was heated
5. 5
   Temperaturto reflux where it
6. 6
   TemperaturThe reaction mixture was then cooled
7. 7
   Filtrationfiltered
8. 8
   WaschenThe filter cake was washed with diethyl ether
9. 9
   ExtraktionThe combination was extracted with two 20 mL portions of aqueous 20% sodium hydroxide
10. 10
    TrocknenThe organic layer was dried with magnesium sulfate
11. 11
    Filtrationfiltered
12. 12
    EinengenThe filtrate was concentrated under reduced pressure to a residual oil
13. 13
    workup.DISTILLATIONThe oil was distilled under vacuum

Vorschrift

Under a nitrogen atmosphere, a solution of 13.6 grams (0.106 mole) of 4-chlorophenol in 50 mL of diglyme was stirred, and 24.1 mL (0.106 mole) of methanolic 25% sodium methoxide was added dropwise. Upon completion of addition, the reaction mixture was heated to about 165° C. to remove methanol. After the methanol was removed, the heating was ceased, and 25.0 grams (0.106 mole) of 1,3-dibromobenzene and 1.3 grams of cuprous bromide were added. Upon completion of the additions, the reaction mixture was heated to reflux where it was stirred for about 21 hours. The reaction mixture was then cooled and filtered. The filter cake was washed with diethyl ether, and the wash was combined with the filtrate. The combination was extracted with two 20 mL portions of aqueous 20% sodium hydroxide and then with two 75 mL portions of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The oil was distilled under vacuum, yielding about 9.0 grams of 3-(4-chlorophenoxy)phenyl bromide, bp 110° C./0.5 mm Hg. The NMR spectrum was consistent with the proposed structure.

Quelle