2,6-Dibromopyridine → 2-Bromo-6-[(oxolan-3-yl)oxy]pyridine

HRID 479666Notes

Reaction equation

HRID 479666 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][O:4][CH2:3]1.[H-].[Na+].[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12](Br)[N:11]=1>C1COCC1>[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:1][CH:2]2[CH2:6][CH2:5][O:4][CH2:3]2)[N:11]=1

Participants

5

Reactant 3

HCID 122742,6-DibromopyridineHCID 24758Sodium hydrideHCID 2733227(S)-(+)-3-Hydroxytetrahydrofuran

Product 1

HCID 187717992-Bromo-6-[(oxolan-3-yl)oxy]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-(+)-3-hydroxy-tetrahydrofuran (0.34 mL, 4.2 mmol) and dry THF (20 mL) was added NaH (0.17 g, 4.2 mmol, 60%) under N2 at RT. After 5 min, added 2,6-dibromopyridine. Stirred at RT for 4 h. Quenched with H2O and extracted with EtOAc. Washed organic layer with saturated NH4Cl, brine, dried (MgSO4) and concentrated in vacuo to give 2-bromo-6-(tetrahydro-furan-3-yloxy)-pyridine as a clear, colorless oil. MS m/z: 245.2 (M+H). Calc'd for C9H10BrNO2—244.09.

Workup

  1. customQuenched with H2O
  2. extractionextracted with EtOAc
  3. dry with materialWashed organic layer with saturated NH4Cl, brine, dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04d41223e81340bd815c31a8a3884132
Source dataset
uspto-grants-2003_11
Patent number
US06645990B2

Reaction notes

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