Ammonium Chloride → 4-bromo-6,7-difluoro-1H-indole

HRID 928657노트

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HRID 928657 반응식
[Br:1][C:2]1[CH:3]=[C:4]([N+:10]([O-])=O)[C:5]([F:9])=[C:6]([F:8])[CH:7]=1.[CH:13]([Mg]Br)=[CH2:14].C1COCC1.[Cl-].[NH4+]>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[C:4]2[C:3]=1[CH:13]=[CH:14][NH:10]2

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 532162185-Bromo-1,2-difluoro-3-nitrobenzeneHCID 178420667HCID 178420667, 화합물

생성물 1

HCID 903842704-bromo-6,7-difluoro-1H-indole수율 12%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-40 °C

실험 절차

A solution (20 mL) of 5-Bromo-1,2-difluoro-3-nitrobenzene (1.19 g, 5.00 mmol) in THF was cooled to −50° C. To this, a 1 M vinylmagnesium bromide/THF solution (15 mL) was added dropwise. After the mixture was stirred at −40° C. for 4 hours, a saturated aqueous ammonium chloride solution was added thereto, and concentrated under reduced pressure. The reaction solution was diluted with ethyl acetate, and after washed with saturated brine, the resultant was dried over anhydrous magnesium sulfate. The resultant was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane) to thus obtain the title compound.

후처리

  1. concentrationconcentrated under reduced pressure
  2. additionThe reaction solution was diluted with ethyl acetate
  3. washafter washed with saturated brine
  4. dry with materialthe resultant was dried over anhydrous magnesium sulfate
  5. concentrationThe resultant was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (hexane)

출처 및 근거

ORD 기록
ord-10a4fb9beb48464aae2122878b586aee
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290487B2

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