Potassium Carbonate → 2-(4-Bromo-2-chloro-6-methylphenoxy)-5-nitropyridine

HRID 1023341

Reaction equation

HRID 1023341 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].Cl[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:8][C:6]1[CH:5]=[C:4]([CH3:9])[C:3]([O:10][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=2)=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 820314-Bromo-6-chloro-o-cresol

Product 1

HCID 673279772-(4-Bromo-2-chloro-6-methylphenoxy)-5-nitropyridineYield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a DMF (30 mL) solution of 2-chloro-4-bromo-6-methylphenol (4.90 g) were added 2-chloro-5-nitropyridine (3.58 g) and K2CO3 (3.12 g) at room temperature. After stirring at 50° C. for 3 hours, the solvent was removed under reduced pressure. To the residue was added water, and extracted with AcOEt. The organic layer was washed with water, saturated aqueous NaCl, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give 2-(4-bromo-2-chloro-6-methylphenoxy)-5-nitropyridine as a brown solid (7.59 g).

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionTo the residue was added water
  3. extractionextracted with AcOEt
  4. washThe organic layer was washed with water, saturated aqueous NaCl
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ab31265ad4554752ba00e1fb55154b71
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Linked notes

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