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

HRID 1451350

반응식

HRID 1451350 반응식
[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

참가 물질

4

반응물 2

HCID 145136N-TriisopropylsilylpyrroleHCID 9834204N-Bromosuccinamide

생성물 1

HCID 27633023-Bromo-1-(triisopropylsilyl)pyrrole수율 58.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4a471699db2c4eebb74bb36690c97b31
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05604224

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