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Water → 2-[2-Chloro-4-(trifluoromethyl)phenoxy]-5-nitropyridine

HRID 2412524
Notes
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Reaction equation

HRID 2412524 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[Cl:7][C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=1[OH:18].Cl[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][N:21]=1.O>CS(C)=O>[N+:26]([C:23]1[CH:22]=[N:21][C:20]([O:18][C:9]2[CH:10]=[CH:11][C:12]([C:14]([F:16])([F:17])[F:15])=[CH:13][C:8]=2[Cl:7])=[CH:25][CH:24]=1)([O-:28])=[O:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 27366032-Chloro-4-(trifluoromethyl)phenol

Product 1

HCID 133704682-[2-Chloro-4-(trifluoromethyl)phenoxy]-5-nitropyridineYield 81.9%

Reagents, catalysts & solvents 1

HCID 679
Dimethyl Sulfoxide
Solvent
2×

Procedure

7.6 g of anhydrous sodium carbonate and 9.8 g of 2-chloro-4-trifluoromethylphenol were added to 20 ml of dimethyl sulfoxide, and a solution having 7.9 g of 2-chloro-5-nitropyridine dissolved in 10 ml of dimethyl sulfoxide was added dropwise thereto at room temperature (i.e., about 20° to 30° C.) while stirring. After completion of the dropwise addition, the mixture was allowed to react at 50° C. for 30 minutes. After completion of the reaction, the reaction product was poured into water, followed by extracting with methylene chloride. The extracted phase was washed with water and dried, and the solvent was then distilled off to obtain 13 g of a crystal. The thus obtained crystal was recrystallized from n-hexane to obtain 9.8 g of a titled compound having a melting point of 69° to 72° C.

Workup

  1. additionwas added dropwise
  2. additionAfter completion of the dropwise addition
  3. customto react at 50° C. for 30 minutes
  4. customAfter completion of the reaction
  5. extractionby extracting with methylene chloride
  6. washThe extracted phase was washed with water
  7. customdried
  8. distillationthe solvent was then distilled off

Sources & evidence

ORD record
ord-92b57840727442d98e8c66fe852aae4f
Source dataset
uspto-grants-1985_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04493730

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes