Potassium Carbonate → 3-Chloro-2-(2,6-dimethyl-4-nitrophenoxy)-5-trifluoromethylpyridine

HRID 1361471Notes

Reaction equation

HRID 1361471 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[CH3:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[C:16]([CH3:23])[C:15]=1[OH:24].C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[Cl:8][C:7]1[C:2]([O:24][C:15]2[C:14]([CH3:13])=[CH:19][C:18]([N+:20]([O-:22])=[O:21])=[CH:17][C:16]=2[CH3:23])=[N:3][CH:4]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 170302,6-Xylenol, 4-nitro-HCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridine

Product 1

HCID 669219343-Chloro-2-(2,6-dimethyl-4-nitrophenoxy)-5-trifluoromethylpyridineYield 121.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

2,3-Dichloro-5-trifluoromethylpyridine (1.04 g), 0.8 g of 2,6-dimethyl-4-nitrophenol, and 0.5 g of potassium carbonate were added to 3 mL of dimethylacetamide, and the mixture was allowed to react at 155 to 165° C. for one hr. The reaction mixture was cooled, ethyl acetate and distilled water were then added thereto, followed by separation and washing with brine. The ethyl acetate layer was concentrated to give 2.01 g of 3-chloro-2-(2,6-dimethyl-4-nitrophenoxy)-5-trifluoromethylpyridine (yield 100%).

Workup

  1. customto react at 155 to 165° C. for one hr
  2. temperatureThe reaction mixture was cooled
  3. distillationethyl acetate and distilled water
  4. additionwere then added
  5. customfollowed by separation
  6. washwashing with brine
  7. concentrationThe ethyl acetate layer was concentrated

Sources & evidence

ORD record
ord-b3494478224d42dc8eda06c02c1cf4e7
Source dataset
uspto-grants-2011_02
Patent number
US07880006B2

Reaction notes

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