Реакция #1884955

Уравнение реакции

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

BBr3

→

product

Выход 55.0%

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

Выход 55.0%

Растворители

CH2Cl2

Условия реакции

Обработка

1. 1
   ДругоеThe reaction was then quenched with water
2. 2
   Экстракцияextracted with ethyl acetate (3×20 mL)
3. 3
   Промывкаwashed with water
4. 4
   Сушкаdried over MgSO4
5. 5
   Другоеevaporated
6. 6
   ДругоеThe residue was purified by flash chromatography (silica gel, hexanes:ethyl acetate=1:1)

Методика

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).

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