Azobisisobutyronitrile → 4-Bromo-2-(bromomethyl)-5-methoxypyridine

HRID 2204331노트

반응식

HRID 2204331 반응식
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][N:5]=[C:4]([CH3:10])[CH:3]=1.C1C(=O)N([Br:18])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.CCOC(C)=O>[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][N:5]=[C:4]([CH2:10][Br:18])[CH:3]=1

참가 물질

7

반응물 4

HCID 6547AzobisisobutyronitrileHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 735548294-Bromo-5-methoxy-2-methylpyridine

생성물 1

HCID 867031384-Bromo-2-(bromomethyl)-5-methoxypyridine

시약·촉매·용매 2

HCID 5943Carbon Tetrachloride용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 4-bromo-5-methoxy-2-methyl-pyridine (Step AL3) (1.9 g, 9.4 mmol), NBS (1.8 g, 9.9 mmol), AIBN (15 mg, 0.094 mmol) and benzoyl peroxide (23 mg, 0.094 mmol) in CCl4 (2 mL) was stirred at rt for 18 h. The reaction mixture was dissolved in EtOAc and extracted with a saturated aqueous solution of NaHCO3, washed with brine, dried (Na2SO4), filtered and concentrated. The crude product was purified by silica gel column chromatography (hexane/EtOAc, 100:0→70:30). ESI-MS: tR=0.90 min, [M+H]+ 281.9 (LC-MS 1).

후처리

  1. extractionextracted with a saturated aqueous solution of NaHCO3
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel column chromatography (hexane/EtOAc, 100:0→70:30)

출처 및 근거

ORD 기록
ord-1b4ec48eec4b4c8f8fa7644ddc043d61
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365576B2

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