反応 #1884954

反応方程式

NaHCO3

BBr3

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

Water

→

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

収率 43.6%

溶媒

CH2Cl2

反応条件

後処理

1. 1
   その他to quench
2. 2
   その他the reaction
3. 3
   抽出extracted with ethyl acetate (3×5 mL)
4. 4
   乾燥dried over MgSO4
5. 5
   その他evaporated
6. 6
   その他The residue was purified with preparative TLC (Hexane:EA=7:3)

実験手順

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).

出典