Iodine → 4-(2-Methylbenzoyl)pyridine

HRID 54993

反応式

HRID 54993 の反応式
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:9].II.[C:12]([C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)#N.C1C[O:23]CC1>CCOCC>[C:12]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:9])(=[O:23])[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1

参加物

7

反応物 5

HCID 807IodineHCID 72362-BromotolueneHCID 75064-CyanopyridineHCID 8028TetrahydrofuranHCID 5462224Magnesium

生成物 1

HCID 199571624-(2-Methylbenzoyl)pyridine

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a warmed mixture of ether (500 mL) and magnesium turnings (14.9 g, 0.614 mol) was added dropwise 2-bromotoluene (105 g, 0.614 mol) and then a crystal of iodine. The reaction mixture was refluxed for 1 hour, then 4-cyanopyridine (30.2 g, 0.29 mol) in THF (130 mL) was added dropwise over 45 minutes. The mixture was refluxed for 1.5 hours, cooled to room temperature and quenched with 6N HCl (200 mL). The organic phase was separated, the aqueous phase was extracted with Et2O, and the combined ether phases were extracted with 2N HCl. The aqueous acidic phases were combined, basified with concentrated NH4OH, extracted with Et2O (3×750 mL) and the combined organic layers were dried over Na2SO4 and the solvent was removed in vacuo to afford 54 g of crude 2-isonicotinoyltoluene.

後処理

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. temperatureThe mixture was refluxed for 1.5 hours
  3. customquenched with 6N HCl (200 mL)
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was extracted with Et2O
  6. extractionthe combined ether phases were extracted with 2N HCl
  7. extractionextracted with Et2O (3×750 mL)
  8. dry with materialthe combined organic layers were dried over Na2SO4
  9. customthe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-b9c36476f8004ffbbff6548013a1af0c
出典データセット
uspto-grants-1997_04
特許番号
US05624922

関連ノート

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