Acetone → 2-(6-Bromo-3-pyridyl)-2-propanol

HRID 971104Notes

Reaction equation

HRID 971104 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.C([Li])CCC.[CH3:14][C:15]([CH3:17])=[O:16]>C(OCC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:15]([OH:16])([CH3:17])[CH3:14])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 693532,5-DibromopyridineHCID 178418339Butyllithium

Product 1

HCID 223919732-(6-Bromo-3-pyridyl)-2-propanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2,5-dibromopyridine in diethyl ether (5 ml/mmol) was cooled to −78° C., and n-butyllithium 2.5M in hexanes (1.05 eq) was added slowly. After 2 h in the cold, acetone (1.3 eq) was added and stirring was continued for 1 hour. The resulting mixture was quenched with saturated aqueous ammonium chloride solution, warmed to room temperature, and partitioned between ether and water. The crude product from the organic phase was triturated with 1:1 ether-hexane and filtered to afford the 2-Bromo-5-(1-hydroxy-1-methylethyl)pyridine compound as a solid.

Workup

  1. customThe resulting mixture was quenched with saturated aqueous ammonium chloride solution
  2. custompartitioned between ether and water
  3. customThe crude product from the organic phase was triturated with 1:1 ether-hexane
  4. filtrationfiltered

Sources & evidence

ORD record
ord-bc780fc65c6e47dd96487e817e0799ac
Source dataset
uspto-grants-2007_12
Patent number
US07312334B2

Reaction notes

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