Methyl morpholine oxide → Methyl 3,5-dibromo-4-formylbenzoate

HRID 394205

Reaktionsgleichung

Reaktionsgleichung von HRID 394205
Br[CH2:2][C:3]1[C:12]([Br:13])=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[Br:14].C[N+]1([O-])CC[O:19]CC1>C(#N)C.[Cl-].[Na+].O>[Br:14][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([Br:13])[C:3]=1[CH:2]=[O:19])[C:7]([O:9][CH3:10])=[O:8]

Komponenten

5

Edukt 2

HCID 82029Methyl morpholine oxideHCID 22647948444663-80-32×

Produkt 1

HCID 22647908Methyl 3,5-dibromo-4-formylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Methyl 3,5-dibromo-4-(bromomethyl)benzoate (INTERMEDIATE 24) (3.9 g) was dissolved in acetonitrile (100 mL) and to this was added 4 Å molecular sieves and N-methylmorpholine N-oxide (1.18 g) and the reaction heated to 50° C. for 12 h. The reaction mixture was poured into brine and extracted into ethyl acetate, dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography eluting with 90% hexane:10% ethyl acetate to give the title compound. 1H NMR (500 MHz, CDCl3): δ 10.27 (s, 1H); 8.29 (s, 2H); 3.99 (s, 3H).

Aufarbeitung

  1. extractionextracted into ethyl acetate
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with 90% hexane

Quellen und Nachweise

ORD-Eintrag
ord-552b45866d3a478b82a8275088fb5393
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809199B2

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