3-Nitrophenol → 2-(3-nitrophenoxy)pyrazine

HRID 1696435Notes

Reaction equation

HRID 1696435 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].I[C:14]1[CH:19]=[N:18][CH:17]=[CH:16][N:15]=1>CS(C)=O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][C:14]1[CH:19]=[N:18][CH:17]=[CH:16][N:15]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 111373-NitrophenolHCID 24758Sodium hydrideHCID 642841Iodopyrazine

Product 1

HCID 47843532-(3-nitrophenoxy)pyrazineYield 61%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 3-nitrophenol (0.151 g, 0.733 mmol) in DMSO (5 mL) was added NaH (35 mg of a 60% dispersion, 0.88 mmol) at 0° C. under Ar atmosphere. After stirring for 30 min, 2-iodopyrazine (0.133 mg, 0.953 mmol) was added and mixture heated to 85° C. for 4 h. To the mixture was added satd. NH4Cl solution (25 mL) and the product extracted with EtOAc (2×25 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated to yield a crude residue which was purified by column chromatography to afford (97 mg, 61% yield) 2-(3-nitrophenoxy)pyrazine as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.53 (brs, 1H), 8.38 (d, J=2.4 Hz, 1H), 8.16-8.09 (m, 3H), 7.63 (t, J=8.0 Hz, 1H), 7.57-7.54 (m, 1H); MS (ESI) m/z: 218.0 (M+H+).

Workup

  1. additionTo the mixture was added
  2. extractionNH4Cl solution (25 mL) and the product extracted with EtOAc (2×25 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto yield a crude residue which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-63ebcc2c97f84325b7bf9358778642c7
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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