Benzyl Bromide → 6-(Benzyloxy)-2-chlorobenzo[d]thiazole

HRID 549678Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 549678
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:9][C:10]1[S:11][C:12]2[CH:18]=[C:17]([OH:19])[CH:16]=[CH:15][C:13]=2[N:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC#N.CCOC(C)=O>[CH2:1]([O:19][C:17]1[CH:16]=[CH:15][C:13]2[N:14]=[C:10]([Cl:9])[S:11][C:12]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 147498432-Chlorobenzo[d]thiazol-6-ol

Produkt 1

HCID 596715856-(Benzyloxy)-2-chlorobenzo[d]thiazoleAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Benzyl bromide (0.921 g, 5.39 mmol) was added to a mixture of 2-chlorobenzo[d]thiazol-6-ol (1.00 g, 5.39 mmol) and cesium carbonate (1.76 g, 5.39 mmol) in CH3CN (15 mL). After 2 h at rt, the reaction mixture was heated to 70° C. overnight. Upon cooling to rt, the reaction mixture was diluted with EtOAc (100 mL) and washed with water (3×75 mL) and brine (75 mL). The EtOAc layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The material was purified by column chromatography (0 to 8% EtOAc in Hexanes gradient), yielding 1.396 g (94%) of the title compound as a reddish, waxy solid. LC-MS: RT=10.51 min., [M+H]+=275.9. Rf=0.41 in 10% EtOAc/Hexanes.

Aufarbeitung

  1. temperatureUpon cooling to rt
  2. washwashed with water (3×75 mL) and brine (75 mL)
  3. dry with materialThe EtOAc layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe material was purified by column chromatography (0 to 8% EtOAc in Hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-e4cc59e7b8ff4c5191c4961dc2647148
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943622B2

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