Azobisisobutyronitrile → 2-(Bromomethyl)-3-chlorobenzonitrile

HRID 1886463

반응식

HRID 1886463 반응식
[Cl:1][C:2]1[C:3]([CH3:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[Br:11]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([C:5]#[N:6])[C:3]=1[CH2:10][Br:11]

참가 물질

6

반응물 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 5215083-Chloro-2-methylbenzonitrile

생성물 1

HCID 149805102-(Bromomethyl)-3-chlorobenzonitrile수율 46%

시약·촉매·용매 2

HCID 5943Carbon Tetrachloride용매HCID 6344Dichloromethane용매

실험 절차

To a refluxing solution of 3-chloro-2-methylbenzonitrile (2.0 g, 13.2 mmol) in 20 mL of CCl4 was added 2.6 g (14.4 mmol, 1.1 eq) of N-bromosuccinimide and 0.2 g of AIBN. The solution was refluxed for 3 hours and then cooled, diluted with 500 mL of CH2Cl2 and washed with 200 mL of H2O and 200 mL of brine. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The resultant oil was flash chromatographed with 5:1 hexane/ethyl acetate to yield the titled compound (1.4 g, 46%) as a yellow oil.

후처리

  1. temperatureThe solution was refluxed for 3 hours
  2. temperaturecooled
  3. washwashed with 200 mL of H2O and 200 mL of brine
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customchromatographed with 5:1 hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-4280b87baf5245388b53ad9905af87bd
출처 데이터셋
uspto-grants-1992_09
특허 번호
US05151435

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