Water → 4-(6-Methoxy-naphthalen-2-yloxy)-1-nitrobenzene

HRID 901697Notes

Reaction equation

HRID 901697 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:17][O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[C:24]([OH:29])[CH:23]=[CH:22]2.O>CN(C=O)C>[CH3:17][O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[C:24]([O:29][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1)[CH:23]=[CH:22]2

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 2886346-Methoxy-2-naphthol

Product 1

HCID 669774644-(6-Methoxy-naphthalen-2-yloxy)-1-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 1-fluoro-4-nitrobenzene (10 mmol) in DMF (20 mL) at rt, solid potassium carbonate (30 mmol) was added followed by addition of 6-methoxy-2-naphthol (10 mmol) to the reaction mixture and heating to 80° C. until the reaction was complete as indicated by TLC or HPLC. After cooling to rt, the reaction mixture was poured into H2O (100 mL), extracted with EtOAc (2×50 mL), washed with H2O (2×50 mL) and brine (50 mL), and dried over sodium sulfate. The solvent was removed in vacuuo to afford the desired 4-(6-methoxy-naphthalen-2-yloxy)-1-nitrobenzene. The crude product was used for further transformation.

Workup

  1. temperatureAfter cooling to rt
  2. extractionextracted with EtOAc (2×50 mL)
  3. washwashed with H2O (2×50 mL) and brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed in vacuuo

Sources & evidence

ORD record
ord-a00f0df7a8c246bc96998a3a6c09e836
Source dataset
uspto-grants-2008_04
Patent number
US07361678B2

Reaction notes

Loading…