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Azobisisobutyronitrile → 4-bromo-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one

HRID 1696334
ノート
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反応式

HRID 1696334 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[C:8]([CH3:15])([CH3:14])[CH2:7][CH2:6]2.[Br:16]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:16][CH:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:9](=[O:13])[C:8]([CH3:15])([CH3:14])[CH2:7]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 155786856-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one

生成物 1

HCID 668447194-bromo-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one収率 86%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

To a mixture of 6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one (3.30 g, 16.2 mmol) and 1-bromopyrrolidine-2,5-dione (2.88 g, 16.2 mmol) in 50 mL of CCl4, was added AIBN (0.265 g, 1.62 mmol). The mixture was heated to reflux for three hours. The reaction was cooled to RT and the reaction was quenched with water (25 mL) and extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine, dried over MgSO4 and filtered. The solvent was evaporated and the residue was purified by column chromatography (0-50% EtOAc/Hexane to provide the title compound as a white solid (3.92 g, 86% yield). MS m/z: 284.2 (M+1).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for three hours
  3. customthe reaction was quenched with water (25 mL)
  4. extractionextracted with EtOAc (3×100 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe solvent was evaporated
  9. customthe residue was purified by column chromatography (0-50% EtOAc/Hexane

出典と根拠

ORDレコード
ord-a5caadc7da8d4cf18bef8d681d6d31d4
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08163766B2

反応ノート

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