반응 #1772010

반응 방정식

NaHCO3

BBr3

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

Water

→

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

수율 43.6%

용매

CH2Cl2

반응 조건

후처리

1. 1
   기타to quench
2. 2
   기타the reaction
3. 3
   추출extracted with ethyl acetate (3×5 mL)
4. 4
   건조dried over MgSO4
5. 5
   기타evaporated
6. 6
   기타The residue was purified with preparative TLC (Hexane:EA=7:3)

실험 절차

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).

출처