Reaktion #1884955

Reaktionsgleichung

2-(4′-nitrophenyl)-6-methoxy benzothiazole

BBr3

→

product

Ausbeute 55.0%

2-(4′-Nitrophenyl)-6-hydroxybenzothiazole

Ausbeute 55.0%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was then quenched with water
2. 2
   Extraktionextracted with ethyl acetate (3×20 mL)
3. 3
   Waschenwashed with water
4. 4
   Trocknendried over MgSO4
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe residue was purified by flash chromatography (silica gel, hexanes:ethyl acetate=1:1)

Vorschrift

To a suspension of 2-(4′-nitrophenyl)-6-methoxy benzothiazole (400 mg, 1.5 mmol) in CH2Cl2 (10 mL) was added BBr3 (1M in CH2Cl2, 10 mL, 10 mmol). The reaction mixture was stirred at room temperature for 24 hr. The reaction was then quenched with water, and extracted with ethyl acetate (3×20 mL). The organic layers were combined and washed with water, dried over MgSO4, and evaporated. The residue was purified by flash chromatography (silica gel, hexanes:ethyl acetate=1:1) to give the product as a yellow solid (210 mg, 55%). 1HNMR (300 MHz, Acetone-d6) δ (ppm): 9.02(s, OH), 8.41(d, J=9.1 Hz, 1H), 8.33(d, J=9.1 Hz, 1H), 7.96(d, J=8.6 Hz, 1H), 7.53(d, J=2.4 Hz, 1H), 7.15(dd, J1=8.6 Hz, J2=2.4 Hz, 1H).

Quelle