Methyl iodide → 3-Bromo-4-(methoxymethyl)pyridine

HRID 712636ノート

反応式

HRID 712636 の反応式
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][OH:9].[H-].[Na+].[CH3:12]I>C1COCC1>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][O:9][CH3:12]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 46840038(3-Bromopyridin-4-yl)methanol

生成物 1

HCID 667140503-Bromo-4-(methoxymethyl)pyridine収率 84.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (3-bromo-pyridin-4-yl)-methanol (300 mg, 1.6 mmol) in THF (50 mL) at 0° C. is added 60% NaH (96 mg, 2.4 mmol). Then the mixture is stirred at room temperature for 30 min. MeI (270 mg, 1.9 mmol) is added to the mixture at 0° C. and again the mixture is stirred at room temperature for 4 hrs. Then the reaction is quenched with saturated NH4Cl aqueous solution and the mixture is extracted with EtOAc. The organic layer is separated, dried and concentrated to give the crude product. Purification by prep-TLC affords 274 mg of 3-bromo-4-methoxymethyl-pyridine.

後処理

  1. stirringagain the mixture is stirred at room temperature for 4 hrs
  2. customThen the reaction is quenched with saturated NH4Cl aqueous solution
  3. extractionthe mixture is extracted with EtOAc
  4. customThe organic layer is separated
  5. customdried
  6. concentrationconcentrated
  7. customto give the crude product
  8. customPurification

出典と根拠

ORDレコード
ord-a6443b9e53f24762bc23e1c1fa59505e
出典データセット
uspto-grants-2015_11
特許番号
US09181272B2

反応ノート

読み込み中…