Hydrogen Bromide → 3-Chloro-2-(4-chloro-3-hydroxyphenyl)5-trifluoromethylpyridine

HRID 1957237Notes

Reaction equation

HRID 1957237 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([O:19]C)[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.Br>O>[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([OH:19])[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 157668763-Chloro-2-(4-chloro-3-methoxyphenyl)-5-trifluoromethylpyridine

Product 1

HCID 190687593-Chloro-2-(4-chloro-3-hydroxyphenyl)5-trifluoromethylpyridineYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20.0 g (62.1 mmol) of 3-chloro-2-(4-chloro-3-methoxyphenyl)-5-trifluoromethylpyridine in 110 ml of 47% strength aqueous hydrobromic acid were refluxed for five hours. The reaction mixture was then diluted, while cooling in ice, with about 400 ml of water and extracted three times with 150 ml of methylene chloride each time. The combined organic phases were dried over sodium sulfate and evaporated to give a residue of 17.9 g (94%) of colorless crystals of melting point 105°-107° C.

Workup

  1. additionThe reaction mixture was then diluted
  2. extractionextracted three times with 150 ml of methylene chloride each time
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-08c687409b124e73a89894739d5818b3
Source dataset
uspto-grants-1998_07
Patent number
US05783522

Reaction notes

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