4-Methoxyphenol → 3-(4-Methoxyphenoxy)benzo[b]thiophene

HRID 1386984

反応式

HRID 1386984 の反応式
Br[C:2]1[C:3]2[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=2[S:5][CH:6]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.[Cu]I>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:2]2[C:3]3[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=3[S:5][CH:6]=2)=[CH:15][CH:14]=1

参加物

6

反応物 3

HCID 90154-MethoxyphenolHCID 11430Potassium CarbonateHCID 123250Benzo(b)thiophene, 3-bromo-

生成物 1

HCID 108249753-(4-Methoxyphenoxy)benzo[b]thiophene

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6344Dichloromethane溶媒

反応条件

温度
140 °C

実験手順

A mixture of 4.00 g (19.7 mmol) of 3-bromobenzo[b]thiophene, 4.96 g (40 mmol) of 4-methoxyphenol, 5.52 g (40 mmol) of K2CO3, and 0.20 g (1.0 mmol) of CuI was heated to 140° C. and sonicated at this temperature for 2 h. The reaction was allowed to cool, taken up in CH2Cl2, and the mixture was washed several times with 0.5 N NaOH. The organic layer was dried over Na2SO4 and concentrated in vacuo to an oil that was subjected to chromatography (SiO2; gradient of 0-5% EtOAc in hexanes). The fractions containing the desired product were combined, evaporated in vacuo, and the residue was recrystallized from hexanes to afford 500 mg (1.95 mmol; 10%) of the title compound as a white solid.

後処理

  1. customsonicated at this temperature for 2 h
  2. temperatureto cool
  3. washthe mixture was washed several times with 0.5 N NaOH
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo to an oil that
  6. additionThe fractions containing the desired product
  7. customevaporated in vacuo
  8. customthe residue was recrystallized from hexanes

出典と根拠

ORDレコード
ord-88fa74840acb457dbd2585d04240b8d3
出典データセット
uspto-grants-2001_07
特許番号
US06265575B1

関連ノート

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