Methyl iodide → 5-bromo-2-(methoxymethyl)Pyridine

HRID 1908658ノート

反応式

HRID 1908658 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1.[H-].[Na+].[CH3:12]I>CN(C=O)C.[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][CH3:12])=[N:6][CH:7]=1

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 5200169(5-Bromopyridin-2-yl)methanol

生成物 1

HCID 540443575-bromo-2-(methoxymethyl)Pyridine収率 102.6%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒3 回HCID 57417360Sodium chloride; water溶媒

実験手順

A solution of this (5-bromo-pyridin-2-yl)-methanol (4.80 g, 23.0 mmol) in DMF (25 mL) was added drop wise over 5 minutes to a slurry of sodium hydride (1.10 g, 27.6 mmol) in DMF (50 mL) at 0° C. under N2. The mixture was stirred for 15 minutes before the drop wise addition of a solution of methyl iodide (1.57 mL, 25.3 mmol) in DMF (25 mL). The mixture was allowed to reach room temperature and was then stirred overnight. The mixture was poured into brine and extracted with EtOAc. The combined organic layers were thoroughly washed with brine, dried over MgSO4 and evaporated to dryness to give the title compound as a yellow oil (4.77 g, 98%) sufficiently pure for the next step.

後処理

  1. customto reach room temperature
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were thoroughly washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness

出典と根拠

ORDレコード
ord-0943eab2268d4caa99970f06c3ca237a
出典データセット
uspto-grants-2013_12
特許番号
US08598213B2

反応ノート

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