Ammonium Chloride → 7-bromo-4-fluoro-1H-indole

HRID 387310

반응식

HRID 387310 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[N+:9]([O-])=O.[CH:12]([Mg]Br)=[CH2:13].[NH4+].[Cl-]>C1COCC1.COCCOC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]2[C:3]=1[NH:9][CH:13]=[CH:12]2

참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 27733831-Bromo-4-fluoro-2-nitrobenzeneHCID 178418507HCID 178418507, 화합물

생성물 1

HCID 43429567-bromo-4-fluoro-1H-indole수율 57%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
-78 °C

실험 절차

A solution of 1-bromo-4-fluoro-2-nitrobenzene (3.6 g, 16.4 mmol) in THF (100 mL) was added to a solution of 1 M vinylmagnesium bromide in THF (100 mL, 100 mmol) and DME (100 mL) at −78° C. (bath temp). The reaction was stirred at −78° C. for 4 h, and saturated aqueous NH4Cl was added. The layers were separated, and the organic layer was evaporated. The crude product was purified flash chromatography, giving 2 g (57%) of the title compound.

후처리

  1. customThe layers were separated
  2. customthe organic layer was evaporated
  3. customThe crude product was purified flash chromatography

출처 및 근거

ORD 기록
ord-d7fd7085fa87458d9192a55c5ca7e777
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372875B2

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