1-Chloro-2-nitrobenzene → 7-chloro-2-methyl-1H-indole

HRID 722398노트

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HRID 722398 반응식
[Cl: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>[CH3:13][C:11]1[NH:8][C:3]2[C:4]([CH:12]=1)=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1]

참가 물질

5

반응물 3

HCID 69451-Chloro-2-nitrobenzeneHCID 25517Ammonium ChlorideHCID 178456138HCID 178456138, 화합물

생성물 1

HCID 118160627-chloro-2-methyl-1H-indole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-40 °C

실험 절차

Under a nitrogen atmosphere 42.1 g of 2-chloronitrobenzene are placed in 850 ml of THF. The mixture is cooled to −40° C. and then 1.6 1 of isopropenylmagnesium bromide at 0.5 M in THF are added dropwise. After 1 hour at −40° C. with stirring the mixture is hydrolyzed with 400 ml of saturated NH4Cl solution. The aqueous phase is extracted twice with ether. The organic phase is dried and then evaporated and the residue is chromatographed on silica, eluting with toluene. This gives 20.3 g of the expected compound.

후처리

  1. extractionThe aqueous phase is extracted twice with ether
  2. customThe organic phase is dried
  3. customevaporated
  4. customthe residue is chromatographed on silica
  5. washeluting with toluene

출처 및 근거

ORD 기록
ord-a7ff061a5a104dbba7c8ac314afe138e
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138424B2

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