تفاعل #1884952

معادلة التفاعل

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

BBr3

→

2-(3′-iodo-4′-aminophenyl)-6-hydroxybenzothiazole

المردود 61.1%

المذيبات

CH2Cl2

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   أخرىAfter the reaction was quenched with water
2. 2
   استخلاصThe aqueous layer was extracted with ethyl acetate (3×3 mL)
3. 3
   تجفيفdried over MgSO4
4. 4
   أخرىThe solvent was then evaporated under reduced pressure
5. 5
   أخرىthe residue was purified by preparative TLC (Hexanes:ethyl acetate=7:3)

الإجراء التجريبي

To a solution of 2-(4′-Amino-3′-iodophenyl)-6-methoxy benzothiazole (5) (8.0 mg, 0.02 mmol) in CH2Cl2 (2.0 mL) was injected 1 M BBr3 solution in CH2Cl2 (0.20 ml, 0.20 mmol) under N2 atmosphere. The reaction mixture was stirred at room temperature for 18 hrs. After the reaction was quenched with water, the mixture was neutralized with NaHCO3. The aqueous layer was extracted with ethyl acetate (3×3 mL). The organic layers were combined and dried over MgSO4. The solvent was then evaporated under reduced pressure and the residue was purified by preparative TLC (Hexanes:ethyl acetate=7:3) to give 2-(3′-iodo-4′-aminophenyl)-6-hydroxybenzothiazole (4.5 mg, 58%) as a brown solid. 1HNMR (300 MHz, acetone-d6) δ (ppm): 8.69 (s, 1H), 8.34 (d, J=2.0 Hz, 1H), 7.77 (dd, J1=2.0 Hz, J2=8.4 Hz, 1H), 7.76 (d, J=8.8 Hz, 1H), 7.40 (d, J=2.4 Hz, 1H), 7.02 (dd, J1=2.5 Hz, J2=8.8 Hz, 1H), 6.94 (d, J=8.5 Hz, 1H), 5.47 (br., 2H). HRMS m/z 367.9483 calcd for C13H9N2OSI 367.9480).

المصدر