Bromine → 3-Bromo-4-methylbenzo[d]isothiazole

HRID 502603Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 502603
[SH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[C:4]#[N:5].[Br:11]Br>C(OCC)(=O)C>[Br:11][C:4]1[C:3]2[C:6]([CH3:10])=[CH:7][CH:8]=[CH:9][C:2]=2[S:1][N:5]=1

Komponenten

4

Edukt 2

HCID 24408BromineHCID 162214682-Mercapto-6-methylbenzonitrile

Produkt 1

HCID 574365593-Bromo-4-methylbenzo[d]isothiazoleAusbeute 179,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-mercapto-6-methylbenzonitrile (1.00 g, 6.71 mmol) in ethyl acetate (10 mL), bromine (1.05 g, 6.60 mmol) was added dropwise at 0° C. The reaction mixture was allowed to stir at 0° C. for 3 h. The reaction mixture was then allowed to warm to room temperature, followed by heating at reflux for 3 h. The reaction mixture was concentrated under reduced pressure. Crystallization of the crude mixture with hexanes gave 3-bromo-4-methylbenzo[d]isothiazole (2.7 g), which was carried forward without further purification. MW=228 confirmed by LC-MS, tr=6.82 min (Method E) MH+=229.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. temperatureby heating
  3. temperatureat reflux for 3 h
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customCrystallization of the crude mixture with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-b497cee2fbeb4629abf81dd58a8c2ace
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776847B2

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