Water → 3-Chloro-5-[(5-chloro-3,6-difluoro-2-pyridinyl)oxy]benzonitrile

HRID 1952336Notes

Reaction equation

HRID 1952336 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1.[Cl:11][C:12]1[C:13]([F:20])=[N:14][C:15](F)=[C:16]([F:18])[CH:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([O:10][C:15]2[C:16]([F:18])=[CH:17][C:12]([Cl:11])=[C:13]([F:20])[N:14]=2)[CH:3]=1)[C:8]#[N:9]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27832523-Chloro-2,5,6-trifluoropyridineHCID 219498783-Chloro-5-hydroxybenzonitrile

Product 1

HCID 595297603-Chloro-5-[(5-chloro-3,6-difluoro-2-pyridinyl)oxy]benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-chloro-5-cyanophenol (1-4; 218 mg; 1.41 mmol) and 3-chloro-2,5,6-trifluoropyridine (1-5; 250 mg; 1.49 mmol) in anhydrous DMF (2 mL) was cooled to −40° C. under a nitrogen atmosphere. The reaction mixture was then treated with 260 mg (1.94 mmol) of anhydrous potassium carbonate added in one portion, and the reaction mixture was vigorously stirred and allowed to warm to room temperature slowly over 90 minutes. The reaction mixture was then stirred for another hour at room temperature. The reaction mixture was diluted with a large excess of water, and a thick precipitate formed. After trituration, the suspension was filtered and the solid dried to give the title compound as an off white amorphous solid. 1H NMR (CDCl3): 7.91 (m, 2H), 7.99 (t, 1H), 8.60 (q, 1H). MS M+1=302.

Workup

  1. additionadded in one portion
  2. stirringThe reaction mixture was then stirred for another hour at room temperature
  3. customa thick precipitate formed
  4. filtrationAfter trituration, the suspension was filtered
  5. customthe solid dried

Sources & evidence

ORD record
ord-33da1d600aae494db34bd8cf32b5d5b2
Source dataset
uspto-grants-2013_03
Patent number
US08404856B2

Reaction notes

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