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

HRID 1908658노트

반응식

HRID 1908658 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 540443575-bromo-2-(methoxymethyl)Pyridine수율 102.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매3회HCID 57417360Sodium chloride; water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0943eab2268d4caa99970f06c3ca237a
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598213B2

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