Potassium Carbonate → HCID 178435839, compound

HRID 498959Notes

Reaction equation

HRID 498959 reaction equation
[F:1][C:2]([F:23])([F:22])[CH2:3][S:4][C:5]1[CH:12]=[C:11]([C:13]2[C:14]([C:18]([F:21])([F:20])[F:19])=[N:15][NH:16][CH:17]=2)[CH:10]=[CH:9][C:6]=1[CH:7]=O.[C:24](=O)([O-])[O-].[K+].[K+].O1CCOCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[F:1][C:2]([F:23])([F:22])[CH2:3][S:4][C:5]1[CH:12]=[C:11]([C:13]2[C:14]([C:18]([F:21])([F:20])[F:19])=[N:15][NH:16][CH:17]=2)[CH:10]=[CH:9][C:6]=1[CH:7]=[CH2:24]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 178519430HCID 178519430, compound

Product 1

HCID 178435839HCID 178435839, compoundYield 43.8%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 962WaterSolvent

Procedure

2.83 g (8.0 mmol) of 2-(2,2,2-trifluoroethylthio)-4-(3-trifluoromethylpyrazolyl)benzaldehyde (Compound No. V-275 of the present invention) prepared in the same manner as in Example 8 (9), 2.85 g (8.0 mmol) of methyltriphenylphosphonium bromide and 1.38 g (10.0 mmol) of potassium carbonate were refluxed in a solvent mixture of 20 ml of dioxane and 0.3 ml of water with heating for 5 hours. After cooling down to room temperature, the insolubles were filtered off, and the dioxane was distilled off under reduced pressure. Purification of the residue by silica gel column chromatography afforded 1.23 g of [2-ethenyl-5-(3-trifluoromethylpyrazolyl)phenyl] 2,2,2-trifluoroethyl sulfide (yield 43.8%) as a pale yellow liquid (nD20 1.5328).

Workup

  1. temperaturewith heating for 5 hours
  2. filtrationthe insolubles were filtered off
  3. distillationthe dioxane was distilled off under reduced pressure
  4. customPurification of the residue by silica gel column chromatography

Sources & evidence

ORD record
ord-6b73419f53dc4698a17161e0380e32ca
Source dataset
uspto-grants-2010_08
Patent number
US07767626B2

Reaction notes

Loading…