Phenol → 5-Bromo-2-phenoxypyridine

HRID 640572Notes

Reaction equation

HRID 640572 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[C:9]1([OH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CC(C)([O-])C.[K+]>CS(C)=O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([O:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 693532,5-DibromopyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 223468455-Bromo-2-phenoxypyridineYield 70.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2,5-dibromo pyridine (25 g, 106 mmol), phenol (10.5 g, 111 mmol), potassium tert-butoxide (12.5 g, 111 mmol) and dimethyl sulfoxide (250 mL) was stirred for 4 hours at 160° C. This mixture was cooled to room temperature, and partitioned into ethyl acetate and water. The organic layer was separated, washed with water, dried with anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=10:1) to obtain the title compound (18.7 g, 70%).

Workup

  1. temperatureThis mixture was cooled to room temperature
  2. custompartitioned into ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-09af132fcb234a46a96a0ab28fa7434d
Source dataset
uspto-grants-2010_04
Patent number
US07691882B2

Reaction notes

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