Azobisisobutyronitrile → 6-Bromomethyl-nicotinic acid methyl ester

HRID 131261노트

반응식

HRID 131261 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[Br:12]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.CCCCCC>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1

참가 물질

6

반응물 4

HCID 6547AzobisisobutyronitrileHCID 8058HexaneHCID 67184N-bromobutanimideHCID 231548Methyl 6-methylnicotinate

생성물 1

HCID 127522376-Bromomethyl-nicotinic acid methyl ester수율 35.5%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

To a solution of methyl 6-methylnicotinate (6.3 g) in carbon tetrachloride (100 mL) is added successively N-bromosuccinimide (8.9 g) and 2,2′-azobisisobutyronitrile (342 mg), and the mixture is refluxed under heating for 6 hours. After cooling to room temperature, to the reaction mixture is added n-hexane (300 mL) and the insoluble materials are removed by filtration. The filtrate is concentrated in vacuo and the resultant crude product is purified by column chromatography on silica gel (Solvent; n-hexane:ethyl acetate=10:1) and stirred in n-hexane to give methyl 6-(bromomethyl)nicotinate (3.4 g, yield; 35%) as colorless crystals.

후처리

  1. temperaturethe mixture is refluxed
  2. temperatureunder heating for 6 hours
  3. customthe insoluble materials are removed by filtration
  4. concentrationThe filtrate is concentrated in vacuo
  5. customthe resultant crude product is purified by column chromatography on silica gel (Solvent; n-hexane:ethyl acetate=10:1)

출처 및 근거

ORD 기록
ord-88834c4755c14761a72f39e7f625bef1
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384952B2

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