Carbon Dioxide → HCID 17794256, compound

HRID 1531640Notes

Reaction equation

HRID 1531640 reaction equation
Br[C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[C:4]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[N:3]=1.C([Li])CCC.[C:26](=[O:28])=[O:27].Cl>C(OCC)C.C(OCC)(=O)C.O>[CH3:9][S:8][C:6]1[CH:5]=[C:4]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[N:3]=[C:2]([C:26]([OH:28])=[O:27])[CH:7]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 177838442-Bromo-4-(methylsulfanyl)-6-[3-(trifluoromethyl)phenoxy]pyridineHCID 178418339Butyllithium

Product 1

HCID 17794256HCID 17794256, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 22728543Water ethylacetateSolvent

Procedure

2-bromo-4-methylmercapto-6-[3-(trifluoromethyl)phenoxy] pyridine (5.00 g, 0.0137 mol) was dissolved in about 200 ml of diethyl ether. While cooling in a dry ice-acetone bath in an argon atmosphere, the obtained solution was mixed with n-butyl lithium [9.3 ml (ca. 1.63 M in hexane solution), 0.0137×1.1 mol] and then stirred for about 10 minutes. After the interior of the reactor was replaced with a carbon dioxide gas, the solution was removed from the bath and stirred at room temperature for about one hour. The obtained reaction solution was mixed with about 15 ml of a 4 N aqueous hydrochloric acid solution. The obtained solution was distributed in ethyl acetate-water and then washed with saturated brine. The organic phase separated from the solution was dried with anhydrous sodium sulfate, concentrated and then purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), thereby obtaining an aimed product.

Workup

  1. temperatureWhile cooling in a dry ice-acetone bath in an argon atmosphere
  2. customthe solution was removed from the bath
  3. stirringstirred at room temperature for about one hour
  4. customThe obtained reaction solution
  5. washwashed with saturated brine
  6. customThe organic phase separated from the solution
  7. dry with materialwas dried with anhydrous sodium sulfate
  8. concentrationconcentrated
  9. custompurified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-86332a3f76934eb59d035d6f95d3b6da
Source dataset
uspto-grants-2001_03
Patent number
US06200933B1

Reaction notes

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