Water → 2-Bromo-6-iodo-3-[(4-methoxybenzyl)oxy]pyridine

HRID 70548

Reaction equation

HRID 70548 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Cl)=[CH:11][CH:10]=1.[Br:17][C:18]1[C:23]([OH:24])=[CH:22][CH:21]=[C:20]([I:25])[N:19]=1.O>CN(C)C=O>[Br:17][C:18]1[C:23]([O:24][CH2:13][C:12]2[CH:15]=[CH:16][C:9]([O:8][CH3:7])=[CH:10][CH:11]=2)=[CH:22][CH:21]=[C:20]([I:25])[N:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 109794792-Bromo-6-iodopyridin-3-ol

Product 1

HCID 866580052-Bromo-6-iodo-3-[(4-methoxybenzyl)oxy]pyridineYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (12 g) and 4-methoxybenzyl chloride (8.8 mL) were added to a solution of 2-bromo-6-iodopyridin-3-ol (12 g) in N,N-dimethylformamide (130 mL), and the mixture was stirred at room temperature for six hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:1→0:100) to give 2-bromo-6-iodo-3-[(4-methoxybenzyl)oxy]pyridine as a colorless powder (18 g, 100%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:1→0:100)

Sources & evidence

ORD record
ord-c28d027628f646698aaa0af849896fb1
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Linked notes

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