Sodium Chloride → 7-bromo-2-ethyl-1H-indole

HRID 890235노트

반응식

HRID 890235 반응식
[Mg].Br[C:3]([CH2:5][CH3:6])=[CH2:4].[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-])=O.[Na+].[Cl-]>C1COCC1>[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:9]=1[NH:14][C:3]([CH2:5][CH3:6])=[CH:4]2

참가 물질

6

반응물 4

HCID 5234Sodium ChlorideHCID 113411-Bromo-2-nitrobenzeneHCID 899901-Butene, 2-bromo-2회HCID 5462224Magnesium2회

생성물 1

HCID 222505807-bromo-2-ethyl-1H-indole수율 207.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매4회

반응 조건

온도
60 °C

실험 절차

2.4 g of magnesium are placed in a round-bottomed flask and the magnesium is covered with 10 ml of THF. 1 g of 2-bromo-1-butene, then 10 ml of THF and then again 12.5 g of 2-bromo-1-butene in 30 ml of THF are added. The reaction medium is observed to warm up and then it is heated at 60° C. for 30 minutes after the end of the addition reaction. The mixture is subsequently cooled to −20° C., 20 ml of THF are added and then 6.7 g of 2-bromonitrobenzene are added at −20° C. The mixture is allowed to return to AT. The reaction medium is poured onto 200 ml of a saturated NaCl solution. Extraction is carried out with ether, the extracts are then evaporated and the residue is taken up in DCM. The organic phase is washed with water and then with a saturated NaCl solution. It is dried and evaporated and then the residue is chromatographed on silica while eluting with a cyclohexane/AcOEt (9.5/0.5, v/v) mixture. 3.45 g of the expected compound are obtained.

후처리

  1. temperatureto warm up
  2. additionafter the end of the addition reaction
  3. temperatureThe mixture is subsequently cooled to −20° C.
  4. extractionExtraction
  5. customthe extracts are then evaporated
  6. washThe organic phase is washed with water
  7. customIt is dried
  8. customevaporated
  9. customthe residue is chromatographed on silica
  10. washwhile eluting with a cyclohexane/AcOEt (9.5/0.5

출처 및 근거

ORD 기록
ord-a97595312546450ca0c9737b930206f5
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06995184B2

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