Bromine → Ethyl 5-bromo-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate

HRID 1936857Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1936857
[CH3:1][S:2][C:3]1[S:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]2[CH2:13][CH2:14][CH2:15][C:16](=[O:17])[C:4]=12.[Br:18]Br>C(Cl)(Cl)Cl>[Br:18][CH:15]1[CH2:14][CH2:13][C:5]2=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[S:7][C:3]([S:2][CH3:1])=[C:4]2[C:16]1=[O:17]

Komponenten

4

Edukt 2

HCID 24408BromineHCID 2778748Ethyl 3-(methylthio)-4-oxo-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylate

Produkt 1

HCID 15885619Ethyl 5-bromo-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylateAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

Ethyl 4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate (25.12 g) was dissolved in chloroform (400 ml); a solution of bromine (15.59 g) in chloroform (20 ml) was added dropwise at room temperature over a period of 30 minutes. After the reaction mixture was stirred at room temperature for 40 minutes, it was washed with a 2% aqueous solution of sodium sulfite (400 ml), water, a saturated aqueous solution of sodium hydrogen carbonate and water in that order, and dried (MgSO4), after which the solvent was distilled off to yield ethyl 5-bromo-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate (28.27 g, 87.1%), which was then recrystallized from ethyl acetate-hexane. Light-yellow prisms. Melting point 147-148° C.

Aufarbeitung

  1. washit was washed with a 2% aqueous solution of sodium sulfite (400 ml), water
  2. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and water in that order, and dried (MgSO4)
  3. distillationafter which the solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-c0cf7da274c14554ad3b0ea508014163
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06391905B1

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