N-Triisopropylsilylpyrrole → 3-Bromo-1-(triisopropylsilyl)pyrrole

HRID 1451350

反応式

HRID 1451350 の反応式
[CH:1]([Si:4]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:12])[CH3:11])[N:5]1[CH:9]=[CH:8][CH:7]=[CH:6]1)([CH3:3])[CH3:2].[Br:16]NC(=O)CCC(N)=O>C1COCC1>[Br:16][C:7]1[CH:8]=[CH:9][N:5]([Si:4]([CH:1]([CH3:3])[CH3:2])([CH:10]([CH3:12])[CH3:11])[CH:13]([CH3:15])[CH3:14])[CH:6]=1

参加物

4

反応物 2

HCID 145136N-TriisopropylsilylpyrroleHCID 9834204N-Bromosuccinamide

生成物 1

HCID 27633023-Bromo-1-(triisopropylsilyl)pyrrole収率 58.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 1-triisoproylsilyl-pyrrole (13.2 g,0.059 mol) in 250 ml of THF at -78° C. was added 10.45 g (0.0587 mol) of N-bromosuccinamide (NBS), the mixture was stirred at -78° C. for 3 h. The reaction mixture was warmed to room temperature and concentrated in vacuo, and the resulting residue in hexane was stirred overnight. The hexane solution was filtered through alumina eluting with hexane, the eluent was concentrated in vacuo, and the residue was distilled (b.p. 107°-108° C./0.2 mm) to afford 10.4 g (58.4%) of 3-bromo-1-triisopropylsilyl-pyrrole.

後処理

  1. temperatureThe reaction mixture was warmed to room temperature
  2. concentrationconcentrated in vacuo
  3. stirringthe resulting residue in hexane was stirred overnight
  4. filtrationThe hexane solution was filtered through alumina eluting with hexane
  5. concentrationthe eluent was concentrated in vacuo
  6. distillationthe residue was distilled (b.p. 107°-108° C./0.2 mm)

出典と根拠

ORDレコード
ord-4a471699db2c4eebb74bb36690c97b31
出典データセット
uspto-grants-1997_02
特許番号
US05604224

関連ノート

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