1-Bromo-2-nitrobenzene → 7-Bromo-2-methylindole

HRID 890237노트

반응식

HRID 890237 반응식
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[C:11]([Mg]Br)([CH3:13])=[CH2:12].[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[NH:8][C:11]([CH3:13])=[CH:12]2

참가 물질

5

반응물 3

HCID 113411-Bromo-2-nitrobenzeneHCID 25517Ammonium ChlorideHCID 178456138HCID 178456138, 화합물

생성물 1

HCID 44130817-Bromo-2-methylindole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-55 °C

실험 절차

27.0 g of 2-bromonitrobenzene are placed in 400 ml of THF. The medium is placed under nitrogen and is cooled to −55° C. and then 800 ml of 0.5M isopropenylmagnesium bromide in THF are added dropwise. The medium is left stirring for 1 hour and then it is poured into a saturated NH4Cl solution. Extraction is carried out with ether, the extract is evaporated and then the residue is taken up in DCM. Washing is carried out with a saturated NaCl solution. The organic layer is dried and evaporated and then the residue is chromatographed on silica while eluting with an AcOEt/cyclohexane (1/9, v/v) mixture. 10.7 g of the expected compound are obtained.

후처리

  1. waitThe medium is left
  2. extractionExtraction
  3. customthe extract is evaporated
  4. washWashing
  5. customThe organic layer is dried
  6. customevaporated
  7. customthe residue is chromatographed on silica
  8. washwhile eluting with an AcOEt/cyclohexane (1/9, v/v) mixture

출처 및 근거

ORD 기록
ord-46f31e3bf53946d9b4fc969d470627b5
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06995184B2

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