反应 #1884952

反应方程式

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

BBr3

→

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

收率 61.1%

溶剂

CH2Cl2

CH2Cl2

反应条件

后处理

1. 1
   其他After the reaction was quenched with water
2. 2
   萃取The aqueous layer was extracted with ethyl acetate (3×3 mL)
3. 3
   干燥dried over MgSO4
4. 4
   其他The solvent was then evaporated under reduced pressure
5. 5
   其他the residue was purified by preparative TLC (Hexanes:ethyl acetate=7:3)

实验过程

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).

来源