Water → 2-Nitro-5-phenoxypyridine

HRID 1966205Notes

Reaction equation

HRID 1966205 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[C:11]1[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[N:15][CH:16]=1.O>CN(C=O)C>[N+:17]([C:14]1[CH:13]=[CH:12][C:11]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:16][N:15]=1)([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 24758Sodium hydrideHCID 8176205-Bromo-2-nitropyridine

Product 1

HCID 221794212-Nitro-5-phenoxypyridineYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

8.1 Phenol (25 mmol) is dissolved in DMF (30 ml) and NaH (1.1 eq., 60% suspension in liquid paraffin) is added at 0° C. 5-Bromo-2-nitro-pyridine (1.0 eq.) in DMF (20 ml) is added and stirred 16 h at RT. The reaction solution is poured into water and extracted with ethyl acetate. The combined organic layers are washed with brine, dried over MgSO4 and the solvent is removed in vacuo. 2-Nitro-5-phenoxy-pyridine is obtained after column chromatography (heptan/ethyl acetate) as a brown oil in a yield of 78%; HPLC (method A): 1.95 min; LC-MS: 1.678 min, 217.15 (M+H+).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over MgSO4
  4. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-af9c1f9a2fe449f58beb85ccf789800f
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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