Potassium Carbonate → HCID 65369304, compound

HRID 1409524Notes

Reaction equation

HRID 1409524 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:15]([O:17][CH2:18]Cl)[CH3:16]>CC(C)=O>[Br:1][C:2]1[C:7]([O:8][CH2:18][O:17][CH2:15][CH3:16])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18523Chloromethyl ethyl etherHCID 230702-Bromo-3-pyridinol

Product 1

HCID 65369304HCID 65369304, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a RBF was added 2-bromo-3-pyridinol (6.0 g, 34.5 mmol) and potassium carbonate (11.91 g, 86 mmol) in Acetone (50 mL). The suspension was stirred at ambient temperature for 30 min and then treated with the drop-wise addition of chloromethyl ethyl ether (3.34 mL, 36.7 mmol) via addition funnel. The mixture was stirred at ambient temperature overnight. The mixture was filtered and the filtrate partitioned between EtOAc and water. The combined organic layers were washed with water, saturated solution of sodium bicarbonate and brine, then dried over Mg2SO4 to afford 7.12 g of desired product as a clear oil which was used without further purification.

Workup

  1. stirringThe mixture was stirred at ambient temperature overnight
  2. filtrationThe mixture was filtered
  3. customthe filtrate partitioned between EtOAc and water
  4. washThe combined organic layers were washed with water, saturated solution of sodium bicarbonate and brine
  5. dry with materialdried over Mg2SO4

Sources & evidence

ORD record
ord-78edc630e1644e4796a4b93a67eaea36
Source dataset
uspto-grants-2014_12
Patent number
US08921363B2

Reaction notes

Loading…