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

HRID 1487868노트

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HRID 1487868 반응식
[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]

참가 물질

6

반응물 4

HCID 6547AzobisisobutyronitrileHCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 13614033Methyl 3-iodo-4-methylbenzoate2회

생성물 1

HCID 57446309Methyl 4-(bromomethyl)-3-iodobenzoate수율 78%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

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온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4b1c588599a942a2ba37b6f927d1b774
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428502B2

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