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

HRID 85211

반응식

HRID 85211 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0ef82594ae314ca48f28cdfe6e947d73
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846934B2

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