4-Chlorophenol → HCID 59374031, compound

HRID 473609Notes

Reaction equation

HRID 473609 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[CH:6][CH:7]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(Cl)Cl>CS(C)=O>[Br:1][C:2]1[C:3]([O:16][C:13]2[CH:14]=[CH:15][C:10]([Cl:9])=[CH:11][CH:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 46844-ChlorophenolHCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 6933243-Bromo-2-chloropyridine

Product 1

HCID 59374031HCID 59374031, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-bromo-2-chloropyridine (10 g, 52 mmol), 4-chlorophenol (6.7 g, 52 mmol), cesium carbonate (34 g, 104 mmol) in 100 mL DMSO was heated to 90° C. with stirring overnight. The reaction mixture was dilution with DCM and washed with water and brine. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (0-30% EtOAc/hexane) to provide the title compound.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography (0-30% EtOAc/hexane)

Sources & evidence

ORD record
ord-18c27f219b554c5884a6f2bdd5b484d0
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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