Water → 2-Bromo-6-iodo-3-propoxypyridine

HRID 70546

Reaction equation

HRID 70546 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](I)[CH2:8][CH3:9].[Br:11][C:12]1[C:17]([OH:18])=[CH:16][CH:15]=[C:14]([I:19])[N:13]=1.O>CN(C)C=O>[Br:11][C:12]1[C:17]([O:18][CH2:7][CH2:8][CH3:9])=[CH:16][CH:15]=[C:14]([I:19])[N:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 109794792-Bromo-6-iodopyridin-3-ol

Product 1

HCID 866580042-Bromo-6-iodo-3-propoxypyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (1.38 g) and n-propyl iodide (1.13 g) were added to a solution of 2-bromo-6-iodopyridin-3-ol (1.0 g, described in WO 2007088996) in N,N-dimethylformamide (10 mL), and the mixture was stirred at room temperature for two 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, after which the solvent was evaporated under reduced pressure to give 2-bromo-6-iodo-3-propoxypyridine as a crude product.

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. customafter which the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2d65931bbfa7416b8739f813d3395e7f
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Linked notes

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