Iodine → (4-Methoxyphenyl)(3-methylphenyl)methanone

HRID 1460892

反応式

HRID 1460892 の反応式
[Mg].Br[C:3]1[CH:4]=[C:5]([CH3:9])[CH:6]=[CH:7][CH:8]=1.II.[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#N)=[CH:16][CH:15]=1.[OH:22]S(O)(=O)=O>CCOCC.O>[CH3:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[C:18]([C:17]1[CH:20]=[CH:21][C:14]([O:13][CH3:12])=[CH:15][CH:16]=1)=[O:22]

参加物

8

反応物 5

HCID 807IodineHCID 1118Sulfuric AcidHCID 115603-BromotolueneHCID 701294-MethoxybenzonitrileHCID 5462224Magnesium2 回

生成物 1

HCID 12469466(4-Methoxyphenyl)(3-methylphenyl)methanone収率 73.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

A 3-neck flask equipped with a condenser, mechanical stirrer and dropping funnel is charged under nitrogen with 1.925 g (79.19 g.a.) of magnesium turnings and enough ether to cover the turnings. A few drops of a solution of 3-bromotoluene (15.79 g, 92.28 mmole) in ether (40 mL) is then added along with a crystal of iodine to initiate the reaction. The remainder of the solution is then added dropwise and the mixture is refluxed until most of the magnesium has disappeared. After cooling, a solution of 4-methoxybenzonitrile (10 g, 75.1 mmole, dried in vacuo over P2O5) is added in one portion. The mixture is refluxed for 2 hours (TLC, no starting material present), cooled (ice bath) and slowly treated with cold water (130 mL) followed by dilute H2SO4 (1:1, v/v, 25 mL). The decomposition of the complex is completed by refluxing the mixture for 4 hours (followed by TLC, 8:2 ether-ethyl acetate). Following stirring overnight at room temperature, the layers are separated and extracted with ether (3×). The extracts are washed with 5% NaHCO3, dried (MgSO4) and evaporated to dryness. The crude material (amber oil, 13.93 g) is purified by flash chromatography (on silica Merck-60, eluted with 8:2 petrolether-ethyl acetate) to provide the title compound as a light yellow oil (12.5 g, 73.5%).

後処理

  1. customA 3-neck flask equipped with a condenser, mechanical stirrer
  2. additionis charged under nitrogen with 1.925 g (79.19 g
  3. customthe reaction
  4. additionThe remainder of the solution is then added dropwise
  5. temperatureAfter cooling
  6. temperatureThe mixture is refluxed for 2 hours (TLC
  7. temperatureno starting material present), cooled (ice bath)
  8. customthe layers are separated
  9. extractionextracted with ether (3×)
  10. washThe extracts are washed with 5% NaHCO3
  11. dry with materialdried (MgSO4)
  12. customevaporated to dryness
  13. customThe crude material (amber oil, 13.93 g) is purified by flash chromatography (on silica Merck-60, eluted with 8:2 petrolether-ethyl acetate)

出典と根拠

ORDレコード
ord-6522bed826884085b5f2d73643f7e73c
出典データセット
uspto-grants-1991_12
特許番号
US05071988

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