Toluene → 2-(Benzyloxy)-3-iodo-5-nitropyridine

HRID 42011Notes

Reaction equation

HRID 42011 reaction equation
[I:1][C:2]1[C:3]([OH:11])=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[C:12]1([CH3:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>BrCC1C=CC=CC=1>[CH2:18]([O:11][C:3]1[C:2]([I:1])=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[CH:5][N:4]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 1140TolueneHCID 178526840HCID 178526840, compound

Product 1

HCID 673940512-(Benzyloxy)-3-iodo-5-nitropyridineYield 90%

Reagents, catalysts & solvents 1

HCID 7498Benzyl BromideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-iodo-5-nitropyridin-2-ol (0.011 mol, 3 g) in 30 ml of toluene, 2.5 ml of (bromomethyl)benzene and 5.1 g of Ag2CO3 was added. The mixture was stirred at 70° C. for 6 h. The crude was filtered through Celite and washed with ethyl acetate. The solvent was evaporated affording 3.6 g (yield 90%) of the expected product.

Workup

  1. filtrationThe crude was filtered through Celite
  2. washwashed with ethyl acetate
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-57588fd7330a43c29c9e53395b7d8d3d
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Reaction notes

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