Carbon Dioxide → HCID 21249832, compound

HRID 1531646Notes

Reaction equation

HRID 1531646 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])[CH:5]=[C:4]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[N:3]=1.C([Li])CCC.[C:30](=[O:32])=[O:31].Cl>C(OCC)C.C(OCC)(=O)C.O>[F:11][C:10]([F:13])([F:12])[CH2:9][O:8][C:6]1[CH:5]=[C:4]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[N:3]=[C:2]([C:30]([OH:32])=[O:31])[CH:7]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 21249833HCID 21249833, compoundHCID 178418339Butyllithium

Product 1

HCID 21249832HCID 21249832, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 22728543Water ethylacetateSolvent

Procedure

2-bromo-4-(2,2,2-trifluoroethoxy)-6-[3-(trifluoromethyl)phenoxy] pyridine (9.81 g, 0.0236 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 [16 ml (ca. 1.63 M in hexane solution), 0.0236×1.1 mol]. The obtained mixture was stirred for about 10 minutes. After replacing an interior of the reactor 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, and then distributed in ethyl acetate-water. The organic phase separated from the solution was washed with saturated brine, dried with anhydrous sodium sulfate, concentrated and then purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane). The purified product was recrystallized by adding hexane thereto, 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. customThe organic phase separated from the solution
  6. washwas washed with saturated brine
  7. dry with materialdried with anhydrous sodium sulfate
  8. concentrationconcentrated
  9. custompurified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)
  10. customThe purified product was recrystallized
  11. additionby adding hexane

Sources & evidence

ORD record
ord-996819ffdb084a8fbe519ef1f13bc80f
Source dataset
uspto-grants-2001_03
Patent number
US06200933B1

Reaction notes

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