Isopropanol → 5-Bromo-3-methyl-2-[(propan-2-yl)oxy]pyridine

HRID 2065891Notes

Reaction equation

HRID 2065891 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[CH:10]([OH:13])([CH3:12])[CH3:11]>C([O-])(O)=O.[Na+]>[Br:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([O:13][CH:10]([CH3:12])[CH3:11])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 8176802,5-Dibromo-3-methylpyridine

Product 1

HCID 225911775-Bromo-3-methyl-2-[(propan-2-yl)oxy]pyridine

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of potassium tert. butylate (1.26 g, 11.3 mmol) in isopropanol (30 mL), 2,5-dibromo-3-picoline (2.89 g, 11.3 mmol) is added. The mixture is stirred at 80° C. for 15 h before another portion of potassium tert.-butylate (2.53 g, 27.5 mmol) is added. Stirring is continued at 80° C. for 24 h before the mixture is diluted with sat. aq. NaHCO3-solution. The mixture is extracted with ether, the org. extract is dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 9:1 to give 5-bromo-2-isopropoxy-3-methyl-pyridine (1.24 g) as a colourless oil; LC-MS: tR=1.06 min; [M+1]+=230.00; 1H NMR (CDCl3): δ1.35 (d, J=6.3 Hz, 6H), 2.16 (s, 3H), 5.27 (hept, J=6.3 Hz, 1H), 7.48 (d, J=1.5 Hz, 1H), 8.02 (d, J=2.0 Hz, 1H).

Workup

  1. additionis added
  2. extractionThe mixture is extracted with ether
  3. extractionextract
  4. dry with materialis dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by CC on silica gel eluting with heptane:EA 9:1

Sources & evidence

ORD record
ord-d0705dda5ee54f9bb89a8dc85c035674
Source dataset
uspto-grants-2012_10
Patent number
US08288554B2

Reaction notes

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