反应 #76290

反应方程式

3-iodo-7,9-dimethoxy-10,11-dihydrodibenz[b,f]oxepin-10-one

phenyl boronic acid

potassium carbonate

hydrochloric acid

→

3-phenyl-7,9-dimethoxy-10,11-dihydrodibenz[b,f]oxepin-10-one

收率 31.2%

溶剂

toluene

反应条件

后处理

1. 1
   其他After completion of the reaction
2. 2
   萃取extracted with ethyl acetate
3. 3
   洗涤The organic layer was washed with water
4. 4
   干燥with a saturated sodium chloride aqueous solution and dried with anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
6. 6
   其他The residue was purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=2:1)

实验过程

To 3-iodo-7,9-dimethoxy-10,11-dihydrodibenz[b,f]oxepin-10-one (52) (403 mg, 1.0 mmol), phenyl boronic acid (186 mg, 1.5 mmol), a 2M potassium carbonate aqueous solution (0.6 mL, 1.2 mmol) and tetrakis(triphenylphosphine) palladium (118 mg, 0.10 mmol) was added 5 mL of toluene and stirred at 125° C. for 19 hours. After completion of the reaction, the reaction solution was neutralized with dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and then with a saturated sodium chloride aqueous solution and dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=2:1) to obtain 108 mg (yield 31%) of 3-phenyl-7,9-dimethoxy-10,11-dihydrodibenz[b,f]oxepin-10-one. Demethylation reaction was carried out according to the method of Example 1 to obtain the title compound.

来源