p-Fluoronitrobenzene → 3-Methyl-6-(methyloxy)-1-[(4-nitrophenyl)oxy]-2-phenylnaphthalene

HRID 1992839Notes

Reaction equation

HRID 1992839 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([OH:13])=[C:8]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]([CH3:20])=[CH:6]2.[H-].[Na+].F[C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1>CN(C=O)C>[CH3:20][C:7]1[C:8]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[C:9]([O:13][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[C:10]2[C:5]([CH:6]=1)=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 685363886-Methoxy-3-methyl-2-phenyl-1-naphthol

Product 1

HCID 685397753-Methyl-6-(methyloxy)-1-[(4-nitrophenyl)oxy]-2-phenylnaphthaleneYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Compound 7 (428 mg, 1.62 mmol, 1 equiv) was dissolved in DMF (5 mL) and cooled to 0° C. under N2. Sodium hydride, 60% dispersion (71 mg, 1.78 mmol, 1.1 equiv), followed by 1-fluoro-4-nitrobenzene (457 mg, 3.24 mmol, 2 equiv) were added and the entire reaction mixture was heated to 70° C. for 18 h. The mixture was then partitioned between EtOAc (50 mL) and H2O (50 mL). The organic layer was washed with saturated aqueous NaCl (100 mL), dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by silica gel flash column chromatography (5% EtOAc in hexanes) to provide 37 (490 mg, 78%) as a clear oil. 1HNMR (400 MHz, DMSO-d6): δ 8.03 (m, 2H), 7.76 (s, 1H), 7.53 (m, 1H), 7.38-7.08 (m, 7H), 6.78 (m, 2H), 3.87 (s, 3H), 2.18 (s, 3H). MS m/z 473.3 (M+H)+.

Workup

  1. additionwere added
  2. customthe entire reaction mixture
  3. temperaturewas heated to 70° C. for 18 h
  4. customThe mixture was then partitioned between EtOAc (50 mL) and H2O (50 mL)
  5. washThe organic layer was washed with saturated aqueous NaCl (100 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by silica gel flash column chromatography (5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2eb8e1f7011f4c73be9952f01ed6b810
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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