N-bromobutanimide → 4-(Bromomethyl)-1-fluoro-2-iodobenzene

HRID 1369980노트

반응식

HRID 1369980 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[I:9].[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:10][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([I:9])[CH:4]=1

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 2320234-Fluoro-3-iodotoluene

생성물 1

HCID 185164554-(Bromomethyl)-1-fluoro-2-iodobenzene수율 51.1%

시약·촉매·용매 2

HCID 6547Azobisisobutyronitrile촉매HCID 5943Carbon Tetrachloride용매

실험 절차

4-Fluoro-3-iodotoluene (50 g, 210 mMol), N-bromosuccinimide (37.7 g, 212 mMol) and 2,2′-azobis-(2-methylpropionitrile) (348 mg, 2.12 mMol) were dissolved in carbon tetrachloride (300 mL) under an atmosphere of dry N2. The mixture was heated to reflux for 4 hours and then cooled to ambient temperature. The mixture was concentrated under vacuum and triturated with Et2O. The filtrate was successively washed with water, aqueous saturated NaHCO3 and brine. The ether layer was dried over MgSO4, filtered and concentrated under vacuum to give a red oil. The oil was chromatographed on flash silica gel eluting with hexanes to give 33.8 g of the titled compound as a white solid.

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hours
  3. concentrationThe mixture was concentrated under vacuum
  4. customtriturated with Et2O
  5. washThe filtrate was successively washed with water, aqueous saturated NaHCO3 and brine
  6. dry with materialThe ether layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customto give a red oil
  10. customThe oil was chromatographed on flash silica gel eluting with hexanes

출처 및 근거

ORD 기록
ord-47808013bdee4e72aa7ec309018f45ed
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06579887B2

반응 노트

불러오는 중…