Reaction #1884955

Reaction equation

2-(4′-nitrophenyl)-6-methoxy benzothiazole

BBr3

→

product

Yield 55.0%

2-(4′-Nitrophenyl)-6-hydroxybenzothiazole

Yield 55.0%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   OtherThe reaction was then quenched with water
2. 2
   Extractionextracted with ethyl acetate (3×20 mL)
3. 3
   Washwashed with water
4. 4
   Dryingdried over MgSO4
5. 5
   Otherevaporated
6. 6
   OtherThe residue was purified by flash chromatography (silica gel, hexanes:ethyl acetate=1:1)

Procedure

To a suspension of 2-(4′-nitrophenyl)-6-methoxy benzothiazole (400 mg, 1.5 mmol) in CH2Cl2 (10 mL) was added BBr3 (1M in CH2Cl2, 10 mL, 10 mmol). The reaction mixture was stirred at room temperature for 24 hr. The reaction was then quenched with water, and extracted with ethyl acetate (3×20 mL). The organic layers were combined and washed with water, dried over MgSO4, and evaporated. The residue was purified by flash chromatography (silica gel, hexanes:ethyl acetate=1:1) to give the product as a yellow solid (210 mg, 55%). 1HNMR (300 MHz, Acetone-d6) δ (ppm): 9.02(s, OH), 8.41(d, J=9.1 Hz, 1H), 8.33(d, J=9.1 Hz, 1H), 7.96(d, J=8.6 Hz, 1H), 7.53(d, J=2.4 Hz, 1H), 7.15(dd, J1=8.6 Hz, J2=2.4 Hz, 1H).

Source