Acetone → 2-(5-Bromo-3-pyridyl)propan-2-ol

HRID 445751

Reaction equation

HRID 445751 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.C([Mg]Cl)(C)C.[CH3:14][C:15]([CH3:17])=[O:16]>C1COCC1>[Br:8][C:6]1[CH:7]=[C:2]([C:15]([OH:16])([CH3:17])[CH3:14])[CH:3]=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 693693,5-DibromopyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 223919662-(5-Bromo-3-pyridyl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3,5-dibromopyridine (Aldrich, Buchs, Switzerland, 4.6 mmol) in dry THF under Ar was added slowly a ˜2 M solution of isopropylmagnesium chloride in THF (2.76 ml). The RM was stirred for 2 h at it then was added acetone (6.9 mmol) and the RM was stirred for 2 h at rt. The RM was quenched with brine and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated. The residue was absorbed on silica gel and purified by flash chromatography (heptane/EtOAc 0% to 70%). The fractions containing product were evaporated together to give the title compound as an oil. (HPLC: tR 1.82 min (Method A); M+H=216, 218 MS-ES)

Workup

  1. stirringthe RM was stirred for 2 h at rt
  2. customThe RM was quenched with brine
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was absorbed on silica gel
  9. custompurified by flash chromatography (heptane/EtOAc 0% to 70%)
  10. additionThe fractions containing product
  11. customwere evaporated together

Sources & evidence

ORD record
ord-f91a7bfd6ade4c1e9f7d030c66c68593
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Linked notes

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