Toluene → 2-[(6-bromopyridin-2-yl)oxy]ethanol

HRID 1172643Notes

Reaction equation

HRID 1172643 reaction equation
[CH:1]([O:3][CH2:4][CH2:5][OH:6])=[CH2:2].C1(C)C=CC=CC=1.[H-].[Na+].[Br:16][C:17]1[CH:22]=[CH:21]C=C(Br)[N:18]=1>O>[Br:16][C:17]1[N:18]=[C:1]([O:3][CH2:4][CH2:5][OH:6])[CH:2]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 122742,6-DibromopyridineHCID 12995Hydroxyethyl vinyl etherHCID 24758Sodium hydride

Product 1

HCID 122163092-[(6-bromopyridin-2-yl)oxy]ethanolYield 88.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

8.81 g of ethylene glycol monovinyl ether was added to toluene (100 mL) suspension of 2.4 g of sodium hydride (55% to 72%), and 9.48 g of 2,6-dibromopyridine was added thereto and stirred overnight at 110° C. The reaction liquid was left cooled to room temperature, and water was added thereto to separate the organic layer. This was washed with saturated saline water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. 100 mL of methanol and 576 mg of p-toluenesulfonic acid hydrate were added to the resulting residue, and stirred for 5 hours. After this was concentrated under reduced pressure, aqueous saturated sodium hydrogencarbonate solution was added to it, and extracted with ethyl acetate. This was washed with saturated saline water, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and the resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=9/1 to 2/1) to obtain 7.74 g of the entitled compound as a colorless oily substance.

Workup

  1. additionwas added
  2. customThe reaction liquid
  3. waitwas left
  4. temperaturecooled to room temperature
  5. customto separate the organic layer
  6. washThis was washed with saturated saline water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. addition100 mL of methanol and 576 mg of p-toluenesulfonic acid hydrate were added to the resulting residue
  10. stirringstirred for 5 hours
  11. concentrationAfter this was concentrated under reduced pressure, aqueous saturated sodium hydrogencarbonate solution
  12. additionwas added to it
  13. extractionextracted with ethyl acetate
  14. washThis was washed with saturated saline water
  15. dry with materialdried with anhydrous magnesium sulfate
  16. concentrationconcentrated under reduced pressure
  17. customthe resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=9/1 to 2/1)

Sources & evidence

ORD record
ord-5b9b1dda08d54778975ff1b3fdb480f3
Source dataset
uspto-grants-2010_11
Patent number
US07834019B2

Reaction notes

Loading…