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

HRID 1811851

Reaktionsgleichung

Reaktionsgleichung von HRID 1811851
[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

Komponenten

7

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 178418778HCID 178418778, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-3232732d954a4b738003060783ae6bfc
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362241B2

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