تفاعل #1884954

معادلة التفاعل

NaHCO3

BBr3

2-(4′-methylamino-3′-iodophenyl)-6-methoxy benzothiazole

Water

→

2-(4′-methylamino-3′-iodophenyl)-6-hydroxy benzothiazole

المردود 43.6%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   أخرىto quench
2. 2
   أخرىthe reaction
3. 3
   استخلاصextracted with ethyl acetate (3×5 mL)
4. 4
   تجفيفdried over MgSO4
5. 5
   أخرىevaporated
6. 6
   أخرىThe residue was purified with preparative TLC (Hexane:EA=7:3)

الإجراء التجريبي

To a solution of 2-(4′-methylamino-3′-iodophenyl)-6-methoxy benzothiazole (12 mg, 0.03 mmol) dissolved in CH2Cl2 (4 mL) was added BBr3 (400 μl, 0.4 mmol, 1M in CH2Cl2) under N2. The reaction was allowed to stir at room temperature for 18 hr. Water was then added to quench the reaction and the solution was neutralized with NaHCO3, extracted with ethyl acetate (3×5 mL). The organic layers were combined, dried over MgSO4 and evaporated. The residue was purified with preparative TLC (Hexane:EA=7:3) to give 2-(4′-methylamino-3′-iodophenyl)-6-hydroxy benzothiazole (5 mg, 43%) as brown solid. 1HNMR (300 MHz, CDCl3) δ(ppm): 8.37 (d, H=2.0 Hz, 1H), 7.88 (dd, J1=2.0 Hz, J2=8.4 Hz, 1H), 7.83 (d, J=8.8 Hz, 1H), 7.28 (d, J=2.4 Hz, 1H), 6.96 (dd, J1=2.5 Hz, J2=8.8 Hz, 1H), 6.58 (d, J=8.5 Hz, 1H), 2.96 (s, 3H, CH3).

المصدر