Carbon Dioxide → HCID 178524754, compound

HRID 1428095Notes

Reaction equation

HRID 1428095 reaction equation
C[Li].Br[C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Br:11])[C:9]=1[OH:10].C([Li])CCC.[C:17](=[O:19])=[O:18].Cl>CCOCC.C1COCC1.CCCCCC>[Br:11][C:8]1[C:9]([OH:10])=[C:4]([C:17]([OH:19])=[O:18])[CH:5]=[N:6][CH:7]=1

Participants

9

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 992524-Pyridinol, 3,5-dibromo-2×HCID 178418339ButyllithiumHCID 178418348HCID 178418348, compound

Product 1

HCID 178524754HCID 178524754, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of methyllithium in ether (1 M, 4.8 ml) was added to a solution of 3,5-dibromopyridin-4-ol (1200 mg) in THF (10 ml) at −78° C., and the mixture was stirred for 30 minutes. A solution of n-butyllithium in hexane (1.65 M, 6.0 ml) was added at −78° C., and the mixture was stirred for one hour. Dry ice was added at −78° C. and the mixture was stirred at 0° C. for 20 minutes, followed by addition of a 4 N aqueous hydrochloric acid solution. The precipitated solid was collected by filtration and washed with water to give a mixture of the title compound and 3,5-dibromopyridin-4-ol.

Workup

  1. stirringthe mixture was stirred for one hour
  2. stirringthe mixture was stirred at 0° C. for 20 minutes
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water
  5. customto give

Sources & evidence

ORD record
ord-b012299cc0ab445d951677b042187583
Source dataset
uspto-grants-2015_01
Patent number
US08933103B2

Reaction notes

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