Potassium Carbonate → HCID 66728158, compound
Reaction equation
[Br:1][C:2]1[C:3]([OH:8])=[N:4][CH:5]=[CH:6][CH:7]=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:3]([O:8][CH2:18][O:17][CH2:15][CH3:16])=[N:4][CH:5]=[CH:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a round-bottomed flask was added 3-bromo-2-hydroxypyridine (5 g, 28.7 mmol) and potassium carbonate (9.93 g, 71.8 mmol) in Acetone (300 mL). The suspension was stirred at ambient temperature for 30 min and then treated with the drop-wise addition of chloromethyl ethyl ether (2.78 mL, 30.6 mmol) via addition funnel. The mixture was stirred at ambient temperature overnight. The reaction 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, dried over Mg2SO4, filtered and concentrated. The crude material was to afford 2.46 g of desired product as a clear oil which was used without further purification.
Workup
- stirringThe mixture was stirred at ambient temperature overnight
- filtrationThe reaction mixture was filtered
- customthe filtrate partitioned between EtOAc and water
- washThe combined organic layers were washed with water, saturated solution of sodium bicarbonate and brine
- dry with materialdried over Mg2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c40c5c1b705749a781cf6b3e25a51ead
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921363B2
Reaction notes
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