Potassium Carbonate → HCID 67774932, compound

HRID 873154Notes

Reaction equation

HRID 873154 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[C:4]#[N:5].Cl[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][N:13]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[I:10][C:7]1[CH:8]=[CH:9][C:2]([O:1][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][N:13]=2)=[C:3]([CH:6]=1)[C:4]#[N:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 70230402-Hydroxy-5-iodo-benzonitrile

Product 1

HCID 67774932HCID 67774932, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-hydroxy-5-iodo-benzonitrile (80.0 g, 0.328 mol) and 2-chloro-5-tri fluoromethylpyridine (60.0 g, 0.328 mol) in DMF (500 ml) was added K2CO3 (91.0 g, 0.656 mol). The reaction mixture was refluxed overnight, then filtered and concentrated. Purification via column chromatography on silica gel (petroleum ether/ethyl acetate=10/1) afforded the title product (120 g) as a white solid.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customPurification via column chromatography on silica gel (petroleum ether/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-cb7cc2972c274d11b66b7e46c0b5d5e4
Source dataset
uspto-grants-2015_03
Patent number
US08975400B2

Reaction notes

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