Water → 3-Bromo-5-phenoxypyridine

HRID 1374914Notes

Reaction equation

HRID 1374914 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[C:9]1([OH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.[Cu].C(OCC)C.CCCCCC>[Br:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([O:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=1

Participants

9

Reactant 4

HCID 962WaterHCID 996PhenolHCID 11430Potassium CarbonateHCID 693693,5-Dibromopyridine

Product 1

HCID 232635923-Bromo-5-phenoxypyridine

Reagents, catalysts & solvents 4

HCID 23978CopperCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

3,5-Dibromopyridine (4.74 g), phenol (1.88 g), anhydrous potassium carbonate (3.04 g), copper bronze (0.1 g) in dry N,N-dimethylformamide (20 ml) were stirred under an atmosphere of nitrogen at 145–150° C. for 4.25 hours then cooled and poured into water. The mixture was extracted with diethyl ether (three times), the extracts were combined, washed with water (three times) then dried over magnesium sulphate and evaporated under reduced pressure to give an oil. The oil was fractionated by chromatography (silica; hexane: diethyl ether; 2:1 by volume) to give the required product, 1.70 g, as a colourless oil.

Workup

  1. temperaturethen cooled
  2. extractionThe mixture was extracted with diethyl ether (three times)
  3. washwashed with water (three times)
  4. dry with materialthen dried over magnesium sulphate
  5. customevaporated under reduced pressure
  6. customto give an oil

Sources & evidence

ORD record
ord-b421bdcd40514c39b9dfd617c47b6754
Source dataset
uspto-grants-2007_01
Patent number
US07166621B2

Reaction notes

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