Acetone → 2-(5-Bromopyridin-2-yl)propan-2-ol

HRID 860992Notes

Reaction equation

HRID 860992 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[Li]CCCC.[CH3:14][C:15]([CH3:17])=[O:16]>[NH4+].[Cl-]>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:15]([OH:16])([CH3:17])[CH3:14])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 693532,5-DibromopyridineHCID 178418339Butyllithium

Product 1

HCID 154863922-(5-Bromopyridin-2-yl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
-78 °C

Procedure

To a suspension of 2,5-dibromopyridine (1.0 eq.) in Tol (0.1M) at −78° C. was added dropwise n-BuLi (1.07 eq.). The mixture was stirred at −78° C. for 3 h then acetone (1.2 eq.) was added. The final mixture was stirred for an extra 2 h at −78° C., poured in saturated aqueous NH4Cl and extracted with Tol (2×). The combined organic extracts were dried over Na2SO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 4:1) afforded the title compound as a white solid.

Workup

  1. extractionextracted with Tol (2×)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e305c07986f8409f88118c2a3c7d108c
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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