3,5-Dibromopyridine → 3-Bromo-5-(propan-2-yloxy)pyridine

HRID 2297959Notes

Reaction equation

HRID 2297959 reaction equation
[K].[CH3:2][CH:3]([CH3:5])[O-:4].[K+].Br[C:8]1[CH:9]=[N:10][CH:11]=[C:12]([Br:14])[CH:13]=1>CC(O)C.[Cu]>[Br:14][C:12]1[CH:13]=[C:8]([O:4][CH:3]([CH3:5])[CH3:2])[CH:9]=[N:10][CH:11]=1

Participants

6

Reactant 3

HCID 693693,5-DibromopyridineHCID 5462222PotassiumHCID 23663646Potassium propan-2-olate

Product 1

HCID 105848083-Bromo-5-(propan-2-yloxy)pyridineYield 71.2%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 3776IsopropanolSolvent

Procedure

Potassium metal (6.59 g, 168.84 mmol) was dissolved in dry 2-propanol (60.0 mL) under nitrogen. The resulting potassium isopropoxide was heated with 3,5-dibromopyridine (20.00 g, 84.42 mmol) and copper powder (1 g, 5% by weight of 3,5-dibromopyridine) at 140° C. in a sealed glass tube for 14 h. The reaction mixture was cooled to ambient temperature and extracted with diethyl ether (4×200 mL). The combined ether extracts were dried over sodium sulfate, filtered, and concentrated by rotary evaporation. The resulting crude product was purified by column chromatography over aluminum-oxide, eluting with ethyl acetate-hexane (1:9, v/v). Selected fractions were combined and concentrated by rotary evaporation, producing a pale-yellow oil (12.99 g, 71.2%)

Workup

  1. extractionextracted with diethyl ether (4×200 mL)
  2. dry with materialThe combined ether extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation
  5. customThe resulting crude product was purified by column chromatography over aluminum-oxide
  6. washeluting with ethyl acetate-hexane (1:9, v/v)
  7. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-4fcc9d24a5f640ca8f19555f215b05fc
Source dataset
uspto-grants-2002_12
Patent number
US06492399B1

Reaction notes

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