Sodium Carbonate → 5-Bromo-3-methyl-indol-2-one

HRID 1264487ノート

反応式

HRID 1264487 の反応式
[Br:1]Br.[CH3:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]1=[O:13].C([O-])(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[Br:1][C:10]1[CH:9]=[CH:8][C:7]2[C:12](=[C:4]([CH3:3])[C:5](=[O:13])[N:6]=2)[CH:11]=1

参加物

6

反応物 4

HCID 10340Sodium CarbonateHCID 24408BromineHCID 1509233-MethyloxindoleHCID 517045Sodium Acetate

生成物 1

HCID 220193765-Bromo-3-methyl-indol-2-one収率 93.7%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

Under an atmosphere of nitrogen, bromine (0.96 g, 6.0 mmol) in acetic acid (5 cm3) was added drop wise to a solution of 3-methyl-2-indolinone (0.8749 g, 6.0 mmol) (Kende, et al, Synth. Commun., 12, 1, 1982) and sodium acetate (0.50 g, 6.0 mmol) in acetic acid (10 cm3). The reaction was stirred at room temperature for 3.5 h. Saturated sodium carbonate was added to quench the reaction. The water layer was extracted EtOAc (×3), dried (MgSO4), filtered, and evaporated to give the title compound (1.26 g, 93%), Mp=119-120° C.; 1H NMR (DMSO) δ 1.32 (d, 3H, J=7.66 Hz), 3.45 (q, 1H, J=7.62 Hz), 6.77 (d, 1H, J=8.23 Hz), 7.46 (s, 1H), 7.36-7.33 (m, 1H), 10.4 (s, 1H); IR (KBr) 3200, 1725 cm−1; MS (EI) m/z 224/226 (M−H)−; CHN calculated for C9H8BrNO: C, 47.82; H, 3.57; N, 6.20; Found: C, 47.44; H, 3.42; N, 6.04.

後処理

  1. customto quench
  2. customthe reaction
  3. extractionThe water layer was extracted EtOAc (×3)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-c95ccc701e494e21a385c9c4ceb025de
出典データセット
uspto-grants-2003_04
特許番号
US06544970B2

反応ノート

読み込み中…