Water → 3-Chloro-2-(4-chloro-3-isopropoxyphenyl)-5-trifluoromethylpyridine

HRID 1957240Notes

Reaction equation

HRID 1957240 reaction equation
[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:10])[F:9])[CH:7]=1.[CH:20](I)([CH3:22])[CH3:21].O>CN(C)C=O>[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([O:19][CH:20]([CH3:22])[CH3:21])[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6362Isopropyl iodideHCID 190687593-Chloro-2-(4-chloro-3-hydroxyphenyl)5-trifluoromethylpyridine

Product 1

HCID 190687923-Chloro-2-(4-chloro-3-isopropoxyphenyl)-5-trifluoromethylpyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.23 g (7.8 mmol) of an 80% suspension of sodium hydride in mineral oil was washed with anhydrous pentane to remove the mineral oil and then suspended in 50 ml of anhydrous dimethylformamide. A solution of 2.0 g (6.5 mmol) of 3-chloro-2-(4-chloro-3-hydroxyphenyl)5-trifluoromethylpyridine in 50 ml of anhydrous dimethylformamide was added dropwise to this suspension at 0° C. After the addition is complete, the mixture was stirred for 15 minutes and then 1.3 g (7.8 mmol) of isopropyl iodide were slowly added dropwise. The mixture was then stirred at 20°-25° C. for about 15 h and subsequently poured into 400 ml of water and extracted three times with methyl tert-butyl ether. The combined organic phases were washed with water, dried over sodium sulfate and evaporated under reduced pressure. Yield: 1.9 g (83%) of a colorless oil.

Workup

  1. wash0.23 g (7.8 mmol) of an 80% suspension of sodium hydride in mineral oil was washed with anhydrous pentane
  2. customto remove the mineral oil
  3. additionAfter the addition
  4. stirringThe mixture was then stirred at 20°-25° C. for about 15 h
  5. extractionextracted three times with methyl tert-butyl ether
  6. washThe combined organic phases were washed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e1672e4007fe4aa2a0010870eade1f24
Source dataset
uspto-grants-1998_07
Patent number
US05783522

Reaction notes

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