Cesium carbonate → HCID 66872384, compound

HRID 1967553Notes

Reaction equation

HRID 1967553 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[F:7][C:8]1[CH:13]=[CH:12][C:11]([SH:14])=[CH:10][CH:9]=1.I[C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19]([OH:21])=[O:20]>[Cu]=O.CN1CCCC1=O>[F:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][C:16]2[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=2)[C:19]([OH:21])=[O:20])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 120603-Iodobenzoic acidHCID 677894-Fluorothiophenol

Product 1

HCID 66872384HCID 66872384, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

Copper(II) oxide (4.01 g) and cesium carbonate (19.7 g) were added in that order to an N-methylpyrrolidinone (100 mL) solution of 4-fluorobenzenethiol (3.10 g) and 3-iodobenzoic acid (5.00 g), and stirred overnight at 160° C. After left cooled, the solid in the reaction solution was removed through filtration. 1 M hydrochloric acid was added to the filtrate, extracted three times with ethyl acetate and dried with sodium sulfate. The drying agent was removed through filtration, and the solvent was evaporated off under reduced pressure. The residue was suspended in a mixed solvent of chloroform/hexane, and the solid was collected through filtration to give the intended product (4.08 g, 82%) as a white solid.

Workup

  1. waitAfter left
  2. temperaturecooled
  3. customthe solid in the reaction solution was removed through filtration
  4. addition1 M hydrochloric acid was added to the filtrate
  5. extractionextracted three times with ethyl acetate
  6. dry with materialdried with sodium sulfate
  7. customThe drying agent was removed through filtration
  8. customthe solvent was evaporated off under reduced pressure
  9. filtrationthe solid was collected through filtration

Sources & evidence

ORD record
ord-178741c2f22247129191bb5f8624ceff
Source dataset
uspto-grants-2013_04
Patent number
US08420823B2

Reaction notes

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