Azobisisobutyronitrile → Methyl 4-(bromomethyl)-3-iodobenzoate

HRID 1487868ノート

反応式

HRID 1487868 の反応式
[I:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].C1C(=O)N([Br:20])C(=O)C1.N(C(C)(C)C#N)=NC(C)(C)C#N.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[I:1]

参加物

6

反応物 4

HCID 6547AzobisisobutyronitrileHCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 13614033Methyl 3-iodo-4-methylbenzoate2 回

生成物 1

HCID 57446309Methyl 4-(bromomethyl)-3-iodobenzoate収率 78%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

反応条件

温度
70 °C

実験手順

Into a 100-mL round-bottom flask, was placed a mixture of methyl 3-iodo-4-methylbenzoate (compound 5.3, 3.00 g, 10.9 mmol) in CCl4 (50 mL), NBS (2.9 g, 16.3 mmol), azobisisobutyronitrile (360 mg, 2.19 mmol) and potassium carbonate (1.65 g, 11.9 mmol). The resulting mixture was stirred overnight at 70° C., then cooled to room temperature and concentrated under reduced pressure. The residue was diluted with EtOAc (100 mL) and the mixture was washed with brine (2×50 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:20) as the eluent to yield 3.0 g (78%) of the title compound as a yellow solid.

後処理

  1. customInto a 100-mL round-bottom flask, was placed
  2. temperaturecooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted with EtOAc (100 mL)
  5. washthe mixture was washed with brine (2×50 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:20) as the eluent

出典と根拠

ORDレコード
ord-4b1c588599a942a2ba37b6f927d1b774
出典データセット
uspto-grants-2016_08
特許番号
US09428502B2

反応ノート

読み込み中…