2-Bromopyridine → 2-(3-Bromophenoxy)pyridine

HRID 1049921Notes

Reaction equation

HRID 1049921 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[O:15][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 115633-Bromophenol

Product 1

HCID 216166122-(3-Bromophenoxy)pyridineYield 30.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A suspension of 2-bromopyridine (commercially available) (2.0 g, 13.6 mmol), 3-bromophenol (CAS591-20-8) (4.4 g, 24.9 mmol), K2CO3 (5.2 g, 40 mmol) in DMF (30 mL) was stirred at 130° C. for 30 h. The mixture was filtered, concentrated, and purified by column chromatography to give titled compound (1.0 g, 30.3%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-430fde663951413fbf7a618407a6c87e
Source dataset
uspto-grants-2016_07
Patent number
US09382241B2

Reaction notes

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