Reacción #1884955

Ecuación de reacción

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

BBr3

→

product

Rendimiento 55.0%

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

Rendimiento 55.0%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was then quenched with water
2. 2
   Extracciónextracted with ethyl acetate (3×20 mL)
3. 3
   Lavadowashed with water
4. 4
   Secadodried over MgSO4
5. 5
   Otroevaporated
6. 6
   OtroThe residue was purified by flash chromatography (silica gel, hexanes:ethyl acetate=1:1)

Procedimiento

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).

Fuente