Benzyl Bromide → 3-(Benzyloxy)-6-chloro-2-iodopyridine

HRID 269585Notes

Reaction equation

HRID 269585 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([I:8])[C:5]([OH:9])=[CH:4][CH:3]=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]>[Cl:1][C:2]1[N:7]=[C:6]([I:8])[C:5]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 234331586-Chloro-2-iodo-3-hydroxypyridine

Product 1

HCID 587310103-(Benzyloxy)-6-chloro-2-iodopyridine

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Procedure

6-Chloro-2-iodo-3-pyridinol (1.28 g, 5 mmol) and silver carbonate (1.52 g, 5.5 mmol) were dissolved in toluene (25 ml) and benzyl bromide (654 μl, 5.5 mmol) added. The mixture was heated to reflux under nitrogen for 1 hour. After cooling, the mixture was filtered, washed with water (×2), dried (MgSO4) and evaporated to an orange oil which was flash chromatographed eluting with 5% ethyl acetate in isohexane to give the title compound as an oil which crystallised on standing. LC/MS t=3.70, [MH+] 346, 348.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under nitrogen for 1 hour
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. washwashed with water (×2)
  6. dry with materialdried (MgSO4)
  7. customevaporated to an orange oil which
  8. customchromatographed
  9. washeluting with 5% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-cc2f230821184a0291584740dc3b91bb
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

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