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

HRID 52656

反応式

HRID 52656 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 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.

後処理

  1. temperatureat reflux for one hour
  2. extractionThe mixture was then extracted with one 200 mL portion of diethyl ether
  3. dry with materialThe extract was dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was 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-3fbbd22283364d73a3e65ae42d09c7e0
出典データセット
uspto-grants-1997_04
特許番号
US05616718

関連ノート

読み込み中…