Potassium Carbonate → HCID 13514821, compound

HRID 1642207Notes

Reaction equation

HRID 1642207 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[Cl:11][C:12]1[CH:13]=[C:14]([OH:19])[CH:15]=[C:16]([Cl:18])[CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:11][C:12]1[CH:13]=[C:14]([O:19][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH:15]=[C:16]([Cl:18])[CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 115713,5-DichlorophenolHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 13514821HCID 13514821, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-fluoro-1-nitrobenzene (0.7 ml, 6.47 mmol), 3,5-dichloro-phenol (1.56 g, 9.8 mmol) and potassium carbonate (1.35 g, 9.78 mmol) in dimethylformamide (4 ml) was refluxed with stirring for 3 h. After removal of dimethylformamide, the residue was dissolved in ether (20 ml), and washed with sodium hydroxide (5%, 3×20 ml). The organic layers were combined, dried (MgSO4), filtered and evaporated in-vacuo. The product was obtained as a light yellow solid, 0.57 g, 33%. m.p. 78-80° C.; 1H NMR (270 MHz, CDCl3) δ 6.88 (2H, d, J=1.7 Hz, ArHE, ArHG), 7.12 (1H, t, J=1.7 Hz, ArHF), 7.12 (1H, dd, J=1.2, 8.2 Hz, ArHD), 7.32 (1H, td, J=7.4, 1.2 Hz, ArHB), 7.6 (1H, td, J=7.4, 1.7 Hz, ArHC), 8.0 (1H, dd, J=8.2, 1.7 Hz, ArHA).

Workup

  1. temperaturewas refluxed
  2. customAfter removal of dimethylformamide
  3. dissolutionthe residue was dissolved in ether (20 ml)
  4. washwashed with sodium hydroxide (5%, 3×20 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in-vacuo
  8. customThe product was obtained as a light yellow solid, 0.57 g, 33%

Sources & evidence

ORD record
ord-770a2202347e46a7bcea12c351f191be
Source dataset
uspto-grants-2012_02
Patent number
US08119627B2

Reaction notes

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