反应详情

温度

165 °C

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.

1. additionUpon completion of addition
2. customto remove methanol
3. customAfter the methanol was removed
4. temperatureUpon completion of the additions, the reaction mixture was heated
5. temperatureto reflux where it
6. temperatureThe reaction mixture was then cooled
7. filtrationfiltered
8. washThe filter cake was washed with diethyl ether
9. extractionThe combination was extracted with two 20 mL portions of aqueous 20% sodium hydroxide
10. dry with materialThe organic layer was dried with magnesium sulfate
11. filtrationfiltered
12. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
13. distillationThe oil was distilled under vacuum