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

HRID 2204331ノート

反応式

HRID 2204331 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 5943Carbon Tetrachloride溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-1b4ec48eec4b4c8f8fa7644ddc043d61
出典データセット
uspto-grants-2016_06
特許番号
US09365576B2

反応ノート

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