1-Methylimidazole → 3-(2-Pyridinyloxy)phenol

HRID 1424386Notes

Reaction equation

HRID 1424386 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].Br[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.CN1C=CN=C1.C(=O)([O-])[O-].[K+].[K+]>[Cu]I.N1C=CC=CC=1>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[O:2][C:1]1[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 13901-MethylimidazoleHCID 5054ResorcinolHCID 79732-BromopyridineHCID 11430Potassium Carbonate

Product 1

HCID 204557773-(2-Pyridinyloxy)phenol

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1049PyridineSolvent

Conditions

Temperature
140 °C

Procedure

In a first example, a Pt-001 complex, as described herein, was synthesized. Initially, 3-(pyridine-2-yloxy)phenol was synthesized. Under a nitrogen atmosphere, a pressure vessel was charged with a magnetic stir bar, resorcinol (110 mmol), 2-bromopyridine (100 mmol), 1-methylimidazole (5 mmol), and potassium carbonate (200 mmol). Pyridine (80 mL) was added and bubbled with nitrogen for 20 minutes before copper(I) iodide (10 mmol) was added and bubbled 10 minutes further. The vessel was sealed and heated to 140° C. while stirring. After 2 days, the solution was allowed to cool. The solids were then filtered off and rinsed with a 50:50 mixture of toluene and methanol. The filtrate was reduced by rotary evaporation and 150 ml of water containing 10 mL glacial acetic acid was added and shaken vigorously. The water was decanted off and 50 mL of DCM was added, forming an off white precipitate which was collected by vacuum filtration and dried with ether, resulting in the pure product 3-(pyridin-2-yloxy)phenol with a 55% yield.

Workup

  1. customwas synthesized
  2. customInitially, 3-(pyridine-2-yloxy)phenol was synthesized
  3. additionUnder a nitrogen atmosphere, a pressure vessel was charged with a magnetic stir bar
  4. additionwas added
  5. custombubbled 10 minutes further
  6. customThe vessel was sealed
  7. temperatureto cool
  8. filtrationThe solids were then filtered off
  9. washrinsed with a 50:50 mixture of toluene and methanol
  10. customThe filtrate was reduced by rotary evaporation and 150 ml of water containing 10 mL glacial acetic acid
  11. additionwas added
  12. stirringshaken vigorously
  13. customThe water was decanted off
  14. addition50 mL of DCM was added
  15. customforming an off white precipitate which
  16. filtrationwas collected by vacuum filtration
  17. dry with materialdried with ether

Sources & evidence

ORD record
ord-7757a748a95048df91b69705911113fe
Source dataset
uspto-grants-2015_01
Patent number
US08927713B2

Reaction notes

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