Dimethylformamide → 2-Bromo-5-ethoxypyridine

HRID 1026335Notes

Reaction equation

HRID 1026335 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.I[CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:10][CH3:11])=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 234368922-Bromo-5-ethoxypyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6-bromopyridin-3-ol (7.58 g), iodoethane (5.23 mL), potassium carbonate (9.03 g), and DMF (80 mL) was stirred at 60° C. for 3 hr. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (7.58 g) as a pale yellow solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c4a47108c9424dc2a4060028387f930c
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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