4-(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)oxyphenol → HCID 21466254, compound

HRID 260785Notes

Reaction equation

HRID 260785 reaction equation
[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[Br-:20].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)(Cl)Cl>[Br:20][C:17]1[CH:18]=[C:13]([O:12][C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:11])([F:9])[F:10])=[CH:5][N:4]=2)[CH:14]=[CH:15][C:16]=1[OH:19]

Participants

4

Reactant 2

HCID 97959974-(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)oxyphenolHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 21466254HCID 21466254, compoundYield 138.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution prepared by dissolving the resulting 2.88 g of 4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenol in 300 ml of chloroform, 4.80 g of tetra-n-butyl ammonium tribromide was slowly added with stirring under room temperature. After 12 hours, the reaction solution was concentrated, and the residue was extracted twice with 100 ml of diethyl ether. Then, the ether layers were combined, washed with water, dried over anhydrous magnesium sulfate and then concentrated to give a crude product. This crude product was subjected to silica gel chromatography to give 2.53 g of 2-bromo-4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenol (yield, 69%).

Workup

  1. customTo a solution prepared
  2. additionwas slowly added
  3. concentrationthe reaction solution was concentrated
  4. extractionthe residue was extracted twice with 100 ml of diethyl ether
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customto give a crude product

Sources & evidence

ORD record
ord-51f43d7bc8f14de0b8c9e7c4b60bb85f
Source dataset
uspto-grants-1996_06
Patent number
US05530015

Reaction notes

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