Salicylaldehyde → 2-[(Pyridin-2-yl)oxy]benzaldehyde

HRID 2260177Notes

Reaction equation

HRID 2260177 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Br[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.[Cu]>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[O:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 3

HCID 6998SalicylaldehydeHCID 79732-BromopyridineHCID 11430Potassium Carbonate

Product 1

HCID 190687272-[(Pyridin-2-yl)oxy]benzaldehydeYield 99.4%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1049PyridineSolvent

Procedure

A solution of 2-hydroxybenzaldehyde (10.00 g, 81.9 mmol), 2-bromopyridine (26.91 g, 170.3 mmol), potassium carbonate (17.54 g, 126.9 mmol), and copper (2.60 g, 40.95 mmol) in pyridine (80 mls) was refluxed for 3 days. The reaction was then cooled to r.t., filtered through Celite, diluted with ethylacetate (500 mls) and washed with water (3×300 mls). The organic was then dried with MgSO4 and concentrated. The resulting residue was chromatographed (silica gel, 9:1 hexanes:ether) to afford 16.21 g (99%) of 2-(2-pyridyloxy)benzaldehyde as a yellow oil.

Workup

  1. filtrationfiltered through Celite
  2. additiondiluted with ethylacetate (500 mls)
  3. washwashed with water (3×300 mls)
  4. dry with materialThe organic was then dried with MgSO4
  5. concentrationconcentrated
  6. customThe resulting residue was chromatographed (silica gel, 9:1 hexanes:ether)

Sources & evidence

ORD record
ord-e32d89ca261f482b9ba48de7164805be
Source dataset
uspto-grants-1995_12
Patent number
US05476873

Reaction notes

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