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

HRID 1940248Notes

Reaction equation

HRID 1940248 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-butylammonium 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-0fa5cfd8cd424d5cbc09e3e26808dc0a
Source dataset
uspto-grants-1997_12
Patent number
US05698702

Reaction notes

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