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1,2-Dibromoethane → methyl 1-(2-bromoethyl)-3-nitro-1H-pyrazole-5-carboxylate

HRID 449687
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HRID 449687 반응식
[N+:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([O:11][CH3:12])=[O:10])[CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[Br:19][CH2:20][CH2:21]Br>CC(C)=O>[Br:19][CH2:20][CH2:21][N:7]1[C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[N:8]1
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참가 물질

5

반응물 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 135452337methyl 3-nitro-1H-pyrazole-5-carboxylate

생성물 1

HCID 66743273methyl 1-(2-bromoethyl)-3-nitro-1H-pyrazole-5-carboxylate수율 50.1%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of methyl 5-nitro-1H-pyrazole-3-carboxylate (5.97 g, 34.9 mmol) in acetone (100 mL) was added potassium carbonate (24.1 g, 174 mmol) and 1,2-dibromoethane (19.7 g, 9.02 ml, 105 mmol) and the resulting solution heated to reflux for 2 h and then stirred at room temperature overnight. The resulting mixture was filtered and concentrated and the residue purified by flash chromatography (silica gel, SF65-400 g, 20% to 70% ethyl acetate in hexanes) to give methyl 1-(2-bromoethyl)-3-nitro-1H-pyrazole-5-carboxylate (4.86 g, 50%) as a light yellow solid.

후처리

  1. temperaturethe resulting solution heated
  2. temperatureto reflux for 2 h
  3. filtrationThe resulting mixture was filtered
  4. concentrationconcentrated
  5. customthe residue purified by flash chromatography (silica gel, SF65-400 g, 20% to 70% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-5be450d83ac6411db0e901afc0129ca2
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08481540B2

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