Benzyl Bromide → 3-Benzyloxy-2-iodopyridine

HRID 55257

Reaction equation

HRID 55257 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[C:9]([I:14])=[N:10][CH:11]=[CH:12][CH:13]=1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O.C(=O)([O-])[O-].[Cs+].[Cs+]>[CH2:15]([O:7][C:8]1[C:9]([I:14])=[N:10][CH:11]=[CH:12][CH:13]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 971792-Iodopyridin-3-ol

Product 1

HCID 199575013-Benzyloxy-2-iodopyridine

Reagents, catalysts & solvents 2

HCID 10796Cesium carbonateCatalystHCID 6228DimethylformamideSolvent

Procedure

152.6 g of potassium carbonate and 15.3 g of cesium carbonate are added to a solution of 122 g of 3-hydroxy-2-iodopyridine and 65.7 ml of benzyl bromide in 1.5 l of dimethylformamide, and the suspension is stirred under argon atmosphere for 20 hours at room temperature. The reaction mixture is filtered, the filter residue is washed with dichloromethane, the filtrate is concentrated by evaporation, and the residue is chromatographed on silica gel with hexane/10-20% ethyl acetate. 146.3 g of 3-benzyloxy-2-iodopyridine is obtained as oil.

Workup

  1. filtrationThe reaction mixture is filtered
  2. washthe filter residue is washed with dichloromethane
  3. concentrationthe filtrate is concentrated by evaporation
  4. customthe residue is chromatographed on silica gel with hexane/10-20% ethyl acetate

Sources & evidence

ORD record
ord-e2e957f3b549479c94a5f8e24c545d13
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Linked notes

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