Hydrochloric Acid → 4,7-Dibromo-1H-indole

HRID 2361430노트

반응식

HRID 2361430 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[N+:9]([O-])=O.C(=O)=O.[C:15](#N)[CH3:16].C([Mg]Br)=C.[NH4+].[Cl-].Cl>C1COCC1.CCOC(C)=O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]2[C:4]=1[CH:15]=[CH:16][NH:9]2

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 770041,4-Dibromo-2-nitrobenzeneHCID 86587134Acetonitrile dry iceHCID 178418507HCID 178418507, 화합물

생성물 1

HCID 187528584,7-Dibromo-1H-indole수율 47%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-40 °C

실험 절차

To a solution of 1,4-dibromo-2-nitrobenzene (18 g, 64.1 mmol) in THF (200 mL) at −40° C. (dry ice-acetonitrile) was added slowly a solution of vinylmagnesium bromide (1.0 M in THF, 199 mL, 199 mmol). The resulting mixture was stirred at −40° C. for 1.5 h, then was then treated with saturated aqueous NH4Cl (500 mL) and stirred at room temperature for 1 h. HCl (1M) was added to adjust the pH to 7. EtOAc was added and the organic phase was separated, washed with brine, dried and concentrated. The residue was subjected to column chromatography on silica gel (330 g), eluting with EtOAc-hexane (5:95) to provide a light yellow oil which solidified on standing under vacuum. The desired product was obtained as a solid (8.35 g, 47% yield. LCMS showed one major peak with no ionization.

후처리

  1. stirringstirred at room temperature for 1 h
  2. customthe organic phase was separated
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated
  6. washeluting with EtOAc-hexane (5:95)
  7. customto provide a light yellow oil which

출처 및 근거

ORD 기록
ord-a5aee006fb77407c84420261c894f2bb
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08685969B2

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