Water → 5-Bromo-2-propoxypyridine

HRID 1908656Notes

Reaction equation

HRID 1908656 reaction equation
CC(C)([O-])C.[K+].[Br:7][C:8]1[CH:9]=[CH:10][C:11](Cl)=[N:12][CH:13]=1.[CH2:15]([OH:18])[CH2:16][CH3:17].O>C1COCC1.CCOC(C)=O>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([O:18][CH2:15][CH2:16][CH3:17])=[N:12][CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10311-PropanolHCID 27344145-Bromo-2-chloropyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 233940055-Bromo-2-propoxypyridineYield 97%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

Potassium tert-butoxide (1.85 g, 16.5 mmol) was added to a mixture of 5-bromo-2-chloropyridine (2.89 g, 15.0 mmol) and 1-propanol (1.230 mL, 16.5 mmol) in THF (15 mL). The reaction mixture was heated at 120° C. for 30 minutes in a microwave reactor. The mixture was poured into a mixture of water (50 mL) and EtOAc (100 mL). The organic layer was washed with brine, dried over MgSO4 and evaporated to dryness. Flash chromatography (silica, 0-20% EtOAc in heptanes) gave the title compound as a yellow oil (3.13 g, 97%) sufficiently pure for the next step.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over MgSO4
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-1f720048490641e2a31a3e46e624515c
Source dataset
uspto-grants-2013_12
Patent number
US08598213B2

Reaction notes

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