Dimethylformamide → 3-Chloro-2-(4-chloro-3-propargyloxyphenyl)-5-trifluoromethylpyridine

HRID 1957238Notes

Reaction equation

HRID 1957238 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[Cl:5][C:6]1[C:7]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([OH:23])[CH:17]=2)=[N:8][CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:5][C:6]1[C:7]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([O:23][CH2:3][C:2]#[CH:1])[CH:17]=2)=[N:8][CH:9]=[C:10]([C:12]([F:15])([F:13])[F:14])[CH:11]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 190687593-Chloro-2-(4-chloro-3-hydroxyphenyl)5-trifluoromethylpyridine

Product 1

HCID 190687583-Chloro-2-(4-chloro-3-propargyloxyphenyl)-5-trifluoromethylpyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.73 g (14.6 mmol) of propargyl bromide were added dropwise to a mixture of 3.00 g (9.74 mmol) of 3-chloro-2-(4-chloro-3-hydroxyphenyl)-5-trifluoromethylpyridine, 4.0 g (29 mmol) of potassium carbonate and 100 ml of anhydrous dimethylformamide. The mixture was stirred at 20°-25° C. for about 15 hours and then poured into 400 ml of water. The solution was kept cold for a few hours, and the resulting crystals were then separated off, washed with water and dried under reduced pressure. Yield: 3.1 g (92%) of colorless crystals of melting point 102°-103° C.

Workup

  1. waitThe solution was kept cold for a few hours
  2. customthe resulting crystals were then separated off
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-93bdc64beccd424cb3cb4f5965b2f6f8
Source dataset
uspto-grants-1998_07
Patent number
US05783522

Reaction notes

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