4-Methoxybenzyl alcohol → 3-Bromo-2-fluoro-5-((4-methoxybenzyloxy)methyl)pyridine

HRID 1621439ノート

反応式

HRID 1621439 の反応式
[Br:1][C:2]1[C:3]([F:10])=[N:4][CH:5]=[C:6]([CH2:8]Br)[CH:7]=1.[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][OH:18])=[CH:15][CH:14]=1.[Al]>CC#N.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.[Ag-]=O>[Br:1][C:2]1[C:3]([F:10])=[N:4][CH:5]=[C:6]([CH2:8][O:18][CH2:17][C:16]2[CH:19]=[CH:20][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)[CH:7]=1

参加物

7

反応物 3

HCID 77384-Methoxybenzyl alcoholHCID 5359268AluminumHCID 595482443-Bromo-5-(bromomethyl)-2-fluoropyridine

生成物 1

HCID 595482913-Bromo-2-fluoro-5-((4-methoxybenzyloxy)methyl)pyridine収率 24%

試薬・触媒・溶媒 3

HCID 67553Tetrabutylammonium Iodide触媒HCID 178418778HCID 178418778、化合物触媒HCID 6342Acetonitrile溶媒

実験手順

3-Bromo-5-(bromomethyl)-2-fluoropyridine (5.63 g, 20.9 mmol) was dissolved in MeCN (135 mL) and 4-methoxybenzyl alcohol (5.20 mL, 41.9 mmol), silver (I) oxide (7.169 g, 30.9 mmol), and tetrabutylammonium iodide (2.208 g, 5.98 mmol) were added. The reaction flask was covered with aluminum foil and the reaction was stirred under nitrogen at room temperature overnight. The reaction was filtered through a pad of Celite® (diatomaceous earth), washing with DCM, MeOH and MeCN. The filtrate was concentrated and purified on a silica gel column (3:1 to 2:1 to 3:2 hexanes/DCM to 3:2 DCM/hexanes to 2:1 DCM/hexanes to 3:1 DCM/hexanes to DCM) to give 3-Bromo-2-fluoro-5-((4-methoxybenzyloxy)methyl)pyridine (1.62 g, 24%). MS (ESI pos. ion) m/z 326/328 (M+H)+.

後処理

  1. filtrationThe reaction was filtered through a pad of Celite® (diatomaceous earth)
  2. washwashing with DCM, MeOH and MeCN
  3. concentrationThe filtrate was concentrated
  4. custompurified on a silica gel column (3:1 to 2:1 to 3:2 hexanes/DCM to 3:2 DCM/hexanes to 2:1 DCM/hexanes to 3:1 DCM/hexanes to DCM)

出典と根拠

ORDレコード
ord-ab5a002a5d574e6f8c2231af6515db9c
出典データセット
uspto-grants-2014_07
特許番号
US08772480B2

反応ノート

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