Azobisisobutyronitrile → 2-(Bromomethyl)-1-fluoro-4-nitrobenzene

HRID 85211

反応式

HRID 85211 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].[Br:12]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[F:1]

参加物

5

反応物 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-

生成物 1

HCID 103539672-(Bromomethyl)-1-fluoro-4-nitrobenzene

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

186 g (1.20 mol) of 2-fluoro-5-nitrotoluene are dissolved in 1.2 l of carbon tetrachloride, and 214 g (1.20 mol) of N-bromosuccinimide are added. 19.7 g (120 mmol) of azodiisobutyronitrile are added, and the mixture is heated under reflux. After 16 h, the mixture is allowed to cool, filtered and evaporated to dryness under reduced pressure. The residue is dissolved in 300 ml of dichloromethane, and 300 g of sea sand are added. Once more, the mixture is then concentrated to dryness under reduced pressure, and the residue is applied to a 1 kg silica gel column. The product is chromatographed using a 20:1 mixture of cyclohexane and ethyl acetate, and the product fractions are evaporated to dryness under reduced pressure. The residue is crystallized with cyclohexane and dried under reduced pressure. This gives 92 g (32% of theory) of the desired product.

後処理

  1. temperaturethe mixture is heated
  2. temperatureunder reflux
  3. temperatureto cool
  4. filtrationfiltered
  5. customevaporated to dryness under reduced pressure
  6. dissolutionThe residue is dissolved in 300 ml of dichloromethane
  7. addition300 g of sea sand are added
  8. concentrationOnce more, the mixture is then concentrated to dryness under reduced pressure
  9. customThe product is chromatographed
  10. additiona 20:1 mixture of cyclohexane and ethyl acetate
  11. customthe product fractions are evaporated to dryness under reduced pressure
  12. customThe residue is crystallized with cyclohexane
  13. customdried under reduced pressure

出典と根拠

ORDレコード
ord-0ef82594ae314ca48f28cdfe6e947d73
出典データセット
uspto-grants-2014_09
特許番号
US08846934B2

関連ノート

読み込み中…