Sodium hydride → 1-Methoxy-3-methyl-2-nitro-4-(trifluoromethyl)benzene

HRID 502715

Reaktionsgleichung

Reaktionsgleichung von HRID 502715
[H-].[Na+].[I-].[CH3:4][S+](C)C.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=1[N+:20]([O-:22])=[O:21]>CS(C)=O.C1COCC1>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[C:12]([CH3:4])[C:11]=1[N+:20]([O-:22])=[O:21]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 967482-Nitro-4-trifluoromethylanisole

Produkt 1

HCID 594278831-Methoxy-3-methyl-2-nitro-4-(trifluoromethyl)benzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
15 °C

Versuchsvorschrift

1-methoxy-3-methyl-2-nitro-4-(trifluoromethyl)benzene was prepared by a procedure similar to that described in “Synthesis of 3,6-Disubstituted 2-Nitrotoluenes by Methylation of Aromatic Nitro Compounds with Dimethylsulfonium Methylide”, Kitano, Masafumi, Ohashi Naohito, Synthetic Communications, 30(23), 4247-4254, 2000. To a suspension of NaH (60% by wt. in mineral oil, 362 mg, 9.04 mmol) and trimethylsulfonium iodide (1.84 g, 9.04 mmol) in DMSO (17 ml) and THF (6.7 ml) was added 4-methoxy-3-nitrobenzotrifluoride (1.00 g, 4.52 mmol) as a solution in DMSO (2.7 ml). The reaction mixture was allowed to stir at 10-20° C. for 5 hrs. The reaction mixture was quenched by addition to ice water. The aqueous layer was separated and extracted with toluene 7 times. The combined organic extracts were washed with brine, dried over MgSO4, and filtered. The solvent was removed by distillation at reduced pressure. The residue was purified by automated silica gel chromatography (100% hexanes to 98:2 hexanes:ethylacetate) to provide 1-methoxy-3-methyl-2-nitro-4-(trifluoromethyl)benzene.

Aufarbeitung

  1. custom1-methoxy-3-methyl-2-nitro-4-(trifluoromethyl)benzene was prepared by a procedure similar to
  2. customThe reaction mixture was quenched by addition to ice water
  3. customThe aqueous layer was separated
  4. extractionextracted with toluene 7 times
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe solvent was removed by distillation at reduced pressure
  9. customThe residue was purified by automated silica gel chromatography (100% hexanes to 98:2 hexanes:ethylacetate)

Quellen und Nachweise

ORD-Eintrag
ord-01b80c947a5c4870882a0e0615eb96d4
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776869B2

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