2-Phenoxybenzyl alcohol → 5-Iodo-2-((2-phenoxybenzyl)oxy)pyridine

HRID 384108Notes

Reaction equation

HRID 384108 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][N:3]=1.[O:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][OH:23])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CC(N(C)C)=O>[I:8][C:5]1[CH:6]=[CH:7][C:2]([O:23][CH2:22][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 36601112-Phenoxybenzyl alcoholHCID 43971762-Chloro-5-iodopyridine

Product 1

HCID 684280695-Iodo-2-((2-phenoxybenzyl)oxy)pyridine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-chloro-5-iodopyridine in dimethylacetamide (2 ml), 300 mg of potassium tert-butoxy and 535 mg of (2-phenoxyphenyl)methanol were added, and the reaction solution was stirred at 110° C. for 4 hours. The reaction solution was cooled, then diluted with a saturated saline solution, extracted with diethyl ether, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-10:90)) to afford the title compound as a white solid.

Workup

  1. temperatureThe reaction solution was cooled
  2. additiondiluted with a saturated saline solution
  3. extractionextracted with diethyl ether
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-10:90))

Sources & evidence

ORD record
ord-b5039cb4823e4dc1bcec6c5b7c00649b
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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