Réaction #1772010

Équation de réaction

NaHCO3

BBr3

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

Water

→

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

Rendement 43.6%

Solvants

CH2Cl2

Conditions de réaction

Traitement

1. 1
   Autreto quench
2. 2
   Autrethe reaction
3. 3
   Extractionextracted with ethyl acetate (3×5 mL)
4. 4
   Séchagedried over MgSO4
5. 5
   Autreevaporated
6. 6
   AutreThe residue was purified with preparative TLC (Hexane:EA=7:3)

Mode opératoire

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).

Source