تفاعل #1772011

معادلة التفاعل

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

BBr3

→

product

المردود 55.0%

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

المردود 55.0%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction was then quenched with water
2. 2
   استخلاصextracted with ethyl acetate (3×20 mL)
3. 3
   غسيلwashed with water
4. 4
   تجفيفdried over MgSO4
5. 5
   أخرىevaporated
6. 6
   أخرىThe residue was purified by flash chromatography (silica gel, hexanes:ethyl acetate=1:1)

الإجراء التجريبي

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).

المصدر