Benzyl Bromide → 2-(Benzyloxy)-3-bromo-5-chloropyridine

HRID 269581Notes

Reaction equation

HRID 269581 reaction equation
[Br:1][C:2]1[C:3]([OH:9])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[CH2:10]([O:9][C:3]1[C:2]([Br:1])=[CH:7][C:6]([Cl:8])=[CH:5][N:4]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 178517755HCID 178517755, compound

Product 1

HCID 220583822-(Benzyloxy)-3-bromo-5-chloropyridine

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Procedure

3-Bromo-5-chloro-2-pyridinol (7.0 g, 33.6 mmol) was stirred in toluene (160 ml) and silver carbonate (10.23 g, 36.9 mmol) added, followed by benzyl bromide (6.32 g, 4.39 ml, 36.9 mmol). The mixture was heated to reflux for 1 hour. After cooling, the mixture was filtered, washed with water (×2), dried (MgSO4) and evaporated. The residue was triturated with isohexane and the pale yellow solid filtered and dried. (8.36 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. washwashed with water (×2)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was triturated with isohexane
  9. filtrationthe pale yellow solid filtered
  10. customdried

Sources & evidence

ORD record
ord-d4369e9f678b4d7381f563c85bf92a92
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

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