Water → 2-Bromo-5-[(propan-2-yl)oxy]pyridine

HRID 1748489Notes

Reaction equation

HRID 1748489 reaction equation
Br[CH:2]([CH3:4])[CH3:3].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][N:7]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:2]([CH3:4])[CH3:3])=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 547754082-Bromo-5-[(propan-2-yl)oxy]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromopropane (701 μl) was added to a suspension of 2-bromo-5-hydroxypyridine (1.0 g) and potassium carbonate (2.38 g) in N,N-dimethylformamide (19 ml), and stirred at 80° C. for four hours. Water was added to the reaction solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give the titled compound (1.05 g) as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-fb10f17492554421939177c8f1916cd6
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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