Water → 3-(4-Bromophenoxy)picolinonitrile

HRID 1855286Notes

Reaction equation

HRID 1855286 reaction equation
Cl[C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CS(C)=O>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:2]2[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78084-BromophenolHCID 10796Cesium carbonateHCID 8182583-Chloropyridine-2-carbonitrile

Product 1

HCID 667281343-(4-Bromophenoxy)picolinonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
85 °C

Procedure

A RBF was charged with 3-chloro-2-cyanopyridine (40 g, 289 mmol), 4-bromophenol (49.9 g, 289 mmol) and cesium carbonate (113 g, 346 mmol). The reactants were suspended in 50 mL of DMSO and allowed to stir at 85° C. overnight. The reaction was cooled to RT and 600 mL of water was added to it. The reaction was filtered and the solid washed with water, then air dried to provide 3-(4-bromophenoxy)-picolinonitrile as a tan solid.

Workup

  1. temperatureThe reaction was cooled to RT
  2. filtrationThe reaction was filtered
  3. washthe solid washed with water
  4. customair dried

Sources & evidence

ORD record
ord-7cef60b01e52408ba3542f69a494d034
Source dataset
uspto-grants-2015_02
Patent number
US08962859B2

Reaction notes

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