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

HRID 722399노트

반응식

HRID 722399 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 mixture is placed under nitrogen and cooled to −55° C. and then 800 ml of isopropenylmagnesium bromide at 0.5 M in THF are added dropwise. The mixture is left with stirring for 1 hour and then poured into saturated NH4Cl solution. It is extracted with ether, the extract is evaporated and then the residue is taken up in DCM. It is washed with saturated NaCl solution. It is dried and evaporated and then the residue is chromatographed on silica, eluting with an AcOEt/cyclohexane (1/9; v/v) mixture. This gives 10.7 g of the expected compound.

후처리

  1. waitThe mixture is left
  2. extractionIt is extracted with ether
  3. customthe extract is evaporated
  4. washIt is washed with saturated NaCl solution
  5. customIt is dried
  6. customevaporated
  7. customthe residue is chromatographed on silica
  8. washeluting with an AcOEt/cyclohexane (1/9; v/v) mixture

출처 및 근거

ORD 기록
ord-8995fdecd0bb4973b3c445375ef1fde8
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138424B2

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