4-Methylmorpholine → Methyl 3,5-dibromo-4-{[(phenylsulfanyl)carbonothioyl]oxy}benzoate

HRID 402827

Reaktionsgleichung

Reaktionsgleichung von HRID 402827
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Br:13])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].CN1CCOCC1.Cl[C:22]([S:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[S:23]>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Br:13])[C:11]=1[O:12][C:22]([S:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[S:23])[C:5]([O:7][CH3:8])=[O:6]

Komponenten

6

Edukt 3

HCID 79724-MethylmorpholineHCID 592675Phenyl ChlorodithioformateHCID 726975Methyl 3,5-dibromo-4-hydroxybenzoate

Produkt 1

HCID 77230874Methyl 3,5-dibromo-4-{[(phenylsulfanyl)carbonothioyl]oxy}benzoateAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Methyl 3,5-dibromo-4-hydroxybenzoate (1000 mg, 3.23 mmol) was dissolved in THF (16 mL) and N-methylmorpholine (0.709 mL, 6.45 mmol) was added. The mixture was cooled to 0° C. and phenyl chlorodithioformate (0.549 mL, 3.87 mmol) was added. The mixture was warmed to room temperature and stirred overnight. The mixture was diluted with EtOAc and washed with water. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography (0-15% EtOAc/hexanes) to yield the title compound as a clear oil (1491 mg).

Aufarbeitung

  1. temperatureThe mixture was warmed to room temperature
  2. washwashed with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (0-15% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-719259b39ba4474b81d51115e00d21d3
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742110B2

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