Bromine → 2-Bromo-5-[[3-chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenol

HRID 225004Notes

Reaction equation

HRID 225004 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[O:5][C:6]1[C:11]([Cl:12])=[CH:10][C:9]([C:13]([F:16])([F:15])[F:14])=[CH:8][N:7]=1.[Br:20]Br>C(Cl)(Cl)Cl>[OH:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Br:20])[O:5][C:6]1[C:11]([Cl:12])=[CH:10][C:9]([C:13]([F:16])([F:15])[F:14])=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 27829943-{[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenol

Product 1

HCID 233286762-Bromo-5-[[3-chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenolYield 42.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 150 ml of chloroform, 5.5 g of 2-(3-hydroxyphenoxy)-3-chloro-5-trifluoromethyl pyridine was dissolved and then, 3.5 g of bromine was added dropwise to the solution at a temperature of 10° to 15° C. After the reaction, the reaction product was washed with water, with a sodium bicarbonate aqueous solution, with a saturated sodium thiosulfate solution and then, with water and dried over anhydrous sodium sulfate. Chloroform was distilled off under a reduced pressure and the resulting crystals were washed with hexane and dried to obtain 3.0 g of 2-(3-hydroxy-4-bromophenoxy)-3-chloro-5-trifluoromethyl pyridine having a melting point of 124° to 127° C.

Workup

  1. customAfter the reaction
  2. washthe reaction product was washed with water, with a sodium bicarbonate aqueous solution, with a saturated sodium thiosulfate solution
  3. dry with materialwith water and dried over anhydrous sodium sulfate
  4. distillationChloroform was distilled off under a reduced pressure
  5. washthe resulting crystals were washed with hexane
  6. customdried

Sources & evidence

ORD record
ord-3408868038b944e5b7875bb103e42040
Source dataset
uspto-grants-1980_11
Patent number
US04235621

Reaction notes

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