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

HRID 634531Notes

Reaction equation

HRID 634531 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)phenolYield 55%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
140 °C

Procedure

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 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. 1H NMR (CDCl3): 5.98 (s, 1H), 6.59 (s, 1H), 6.62-6.69 (m, 2H), 6.94 (d, 1H), f 7.02 (dd, 1H), 7.23 (vt, 1H), 7.70 (dd, 1H), 8.23 (b, 1H)

Workup

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

Sources & evidence

ORD record
ord-c64db0bc101847a19e8a3ad27901933a
Source dataset
uspto-grants-2016_04
Patent number
US09324957B2

Reaction notes

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