Azobisisobutyronitrile → 6-Bromomethyl-nicotinic acid methyl ester

HRID 131261

反応式

HRID 131261 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 127522376-Bromomethyl-nicotinic acid methyl ester収率 35.5%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-88834c4755c14761a72f39e7f625bef1
出典データセット
uspto-grants-2008_06
特許番号
US07384952B2

関連ノート

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