Methyl iodide → 6-Bromo-3-hydroxy-3-methylindolin-2-one

HRID 239635

反応式

HRID 239635 の反応式
C[Mg]I.[Mg].[CH3:5]I.[Br:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12](=[O:18])[C:13](=[O:17])[NH:14]2)=[CH:10][CH:9]=1>C(OCC)C.C1COCC1>[Br:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]([OH:18])([CH3:5])[C:13](=[O:17])[NH:14]2)=[CH:10][CH:9]=1

参加物

7

反応物 4

HCID 6328Methyl iodideHCID 957161H-Indole-2,3-dione, 6-bromo-HCID 5462224MagnesiumHCID 178418373HCID 178418373、化合物

生成物 1

HCID 665802586-Bromo-3-hydroxy-3-methylindolin-2-one収率 98.1%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a ice-cold solution of methyl magnesium iodide prepared from magnesium (1.7 g, 70.78 mmoles) and methyl iodide (4.40 ml, 70.78 mmoles) in diethyl ether (60 ml), 6-bromoisatin (4 g, 17.69 mmoles) in THF(120 ml) was added and warmed to room temperature. After 12 h, the reaction mixture was cooled to 0° C., quenched with dilute HCl and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as brown solid (4.2 g, 93% yield). 1H-NMR (δ ppm, CDCl3, 400 MHz): δ 10.34(s,1H), 7.23(t, J=7.9 Hz, 1H), 7.14(dd, J=7.9,1.7 Hz, 1H), 6.93(d, J=1.6 Hz, 1H), 5.92(s, 1H), 1.33(s, 3H).

後処理

  1. additionwas added
  2. temperaturethe reaction mixture was cooled to 0° C.
  3. customquenched with dilute HCl
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-14bd2f7ed9d24323a7d5de36bbe90756
出典データセット
uspto-grants-2014_02
特許番号
US08642607B2

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