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

HRID 1401181Notes

Reaction equation

HRID 1401181 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.C([Li])CCC.[CH3:14][C:15]([CH3:17])=[O:16]>C1(C)C=CC=CC=1>[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-olYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,5-Dibromopyridine (1.04 g, 4.39 mmol) was dissolved in toluene (22 mL) in a 100 mL round-bottomed flask. The mixture was cooled to −78° C. n-Butyllithium (3.02 mL, 4.83 mmol) was added dropwise. The mixture was stirred 30 min, followed by the addition of acetone (2 mL). The mixture was stirred 40 min and then let warm to rt. The mixture was washed with ammonium chloride (5% aq, 50 mL), water (50 mL) and then brine (50 mL). The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by Biotage (16% ethyl acetate in hexanes). Concentration of the desired fractions afforded the product (0.82 g, 3.78 mmol, 86% yield). MS (ESI) m/z 216.0 [M]+, 218.1 [M+2]+.

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred 40 min
  3. washThe mixture was washed with ammonium chloride (5% aq, 50 mL), water (50 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by Biotage (16% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3ced033bb0414b18b04be1cc674c5ad5
Source dataset
uspto-grants-2014_12
Patent number
US08907087B2

Reaction notes

Loading…