2-Fluoropyridine → 2-((4-Bromobenzyl)oxy)pyridine

HRID 1960085Notes

Reaction equation

HRID 1960085 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].F[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1.O.[Cl-].[Na+]>CS(C)=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:7][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 97462-FluoropyridineHCID 701194-Bromobenzyl alcoholHCID 23665647Potassium tert-butoxideHCID 57417360Sodium chloride; water

Product 1

HCID 247991602-((4-Bromobenzyl)oxy)pyridineYield 97.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-bromobenzyl alcohol (18 g, 94.3 mmol) in dimethylsulfoxide (85 mL) was added potassium tert-butoxide (11.5 g, 99 mmol) little by little under a nitrogen atmosphere at room temperature, which was stirred for 10 minutes. To this solution was added 2-fluoropyridine (12.3 g, 123 mmol) dropwise over 30 minutes under a water bath cooling. After stirring at room temperature for two hours, ethyl acetate and 5% sodium chloride water were added, and extracted. After the organic layer was washed sequentially with water and 5% sodium chloride water, the solvent was evaporated under a reduced pressure, so as to obtain the title compound (24.3 g) as a yellow oily product.

Workup

  1. temperaturecooling
  2. stirringAfter stirring at room temperature for two hours
  3. extractionextracted
  4. washAfter the organic layer was washed sequentially with water and 5% sodium chloride water
  5. customthe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-e14090f0160c4d018829c2b299a4f264
Source dataset
uspto-grants-2013_04
Patent number
US08410277B2

Reaction notes

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