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

HRID 1369980ノート

反応式

HRID 1369980 の反応式
[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

参加物

5

反応物 2

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

生成物 1

HCID 185164554-(Bromomethyl)-1-fluoro-2-iodobenzene収率 51.1%

試薬・触媒・溶媒 2

HCID 6547Azobisisobutyronitrile触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-47808013bdee4e72aa7ec309018f45ed
出典データセット
uspto-grants-2003_06
特許番号
US06579887B2

反応ノート

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