Water → 2-Bromo-3-cyclohexyloxy pyridine

HRID 496809

Reaction equation

HRID 496809 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][N:5]=1.Br[CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.O>CN(C)C=O>[Br:3][C:4]1[C:9]([O:10][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7960Cyclohexyl bromideHCID 230702-Bromo-3-pyridinolHCID 24758Sodium hydride

Product 1

HCID 223233602-Bromo-3-cyclohexyloxy pyridineYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (160 mg) was dissolved in dimethylformamide (5 ml) and 2-bromo-3-pyridinol (500 mg) dissolved in dimethylformamide is slowly added dropwise. Then, bromocyclohexane (0.7 ml) was added to the solution and reacted for 5 hours at room temperature. Water was added to the suspension to dilute and extracted with ethyl acetate to separate an organic layer. The separated organic layer was dried with anhydrous magnesium sulfate and distilled under reduced pressure. As a result, 2-bromo-3-cyclohexyloxy pyridine (220 mg, yield: 30%) was obtained as an oil phase.

Workup

  1. additionis slowly added dropwise
  2. customreacted for 5 hours at room temperature
  3. additionto dilute
  4. extractionextracted with ethyl acetate
  5. customto separate an organic layer
  6. dry with materialThe separated organic layer was dried with anhydrous magnesium sulfate
  7. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-048d469ce30545f59c35fb3fe46cfc7d
Source dataset
uspto-grants-2005_09
Patent number
US06946558B2

Linked notes

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