반응 #80934

반응 방정식

4-bromo-2,3-dihydro-2,2-dimethylbenzofuran

potassium persulfate

→

4-bromo-2,3-dihydro-2,2-dimethyl-3-benzofuranone

수율 67.0%

용매

water

acetonitrile

water

반응 조건

후처리

1. 1
   온도at reflux for one hour
2. 2
   추출The mixture was then extracted with one 200 mL portion of diethyl ether
3. 3
   건조The extract was dried with magnesium sulfate
4. 4
   여과filtered
5. 5
   농축The filtrate was concentrated under reduced pressure to a residual oil
6. 6
   세척Elution
7. 7
   농축concentrated under reduced pressure

실험 절차

Under a nitrogen atmosphere, a stirred solution of 3.0 grams (0.013 mole) 4-bromo-2,3-dihydro-2,2-dimethylbenzofuran, 10.7 grams (0.039 mole) of potassium persulfate, and 3.3 grams (0.013 mole) of copper(II) sulfate pentahydrate in 30 mL of water and 30 mL of acetonitrile was heated at reflux for one hour. After this time the reaction mixture was poured into 200 mL of water. The mixture was then extracted with one 200 mL portion of diethyl ether. The extract was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The oil was subjected to column chromatography on silica gel. Elution was accomplished using 1:1 petroleum ether and methylene chloride. The product-containing fractions were combined and concentrated under reduced pressure, yielding 2.1 grams of 4-bromo-2,3-dihydro-2,2-dimethyl-3-benzofuranone. The NMR spectrum was consistent with the proposed structure. Steps A through C were repeated.

출처