Reaction #1772010

Reaction equation

NaHCO3

BBr3

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

Water

→

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

Yield 43.6%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   Otherto quench
2. 2
   Otherthe reaction
3. 3
   Extractionextracted with ethyl acetate (3×5 mL)
4. 4
   Dryingdried over MgSO4
5. 5
   Otherevaporated
6. 6
   OtherThe residue was purified with preparative TLC (Hexane:EA=7:3)

Procedure

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