Potassium Persulfate → 4-Bromo-2,3-dihydro-2,2-dimethyl-3-benzofuranone

HRID 233605

反応式

HRID 233605 の反応式
[Br:1][C:2]1[C:7]2[CH2:8][C:9]([CH3:12])([CH3:11])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.S(OOS([O-])(=O)=O)([O-])(=O)=[O:14].[K+].[K+]>O.C(#N)C.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[Br:1][C:2]1[C:7]2[C:8](=[O:14])[C:9]([CH3:12])([CH3:11])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 2

HCID 24412Potassium PersulfateHCID 539891274-Bromo-2,2-dimethyl-2,3-dihydrobenzofuran

生成物 1

HCID 543779064-Bromo-2,3-dihydro-2,2-dimethyl-3-benzofuranone収率 67%

試薬・触媒・溶媒 3

HCID 24463Copper sulfate pentahydrate触媒HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒

実験手順

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 is heated at reflux for one hour. After this time the reaction mixture is poured into 200 mL of water. The mixture is then extracted with one 200 mL portion of diethyl ether. The extract is dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure to a residual oil. The oil is subjected to column chromatography on silica gel. Elution is accomplished using 1:1 petroleum ether and methylene chloride. The product-containing fractions are combined and concentrated under reduced pressure, yielding 2.1 grams of 4-bromo-2,3-dihydro-2,2-dimethyl-3-benzofuranone. The NMR spectrum is consistent with the proposed structure.

後処理

  1. temperatureat reflux for one hour
  2. extractionThe mixture is then extracted with one 200 mL portion of diethyl ether
  3. dry with materialThe extract is dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated under reduced pressure to a residual oil
  6. washElution
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-716fca5737634edf92985c70a3636402
出典データセット
uspto-grants-1997_01
特許番号
US05593998

関連ノート

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