Réaction #1772011

Équation de réaction

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

BBr3

→

product

Rendement 55.0%

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

Rendement 55.0%

Solvants

CH2Cl2

Conditions de réaction

Traitement

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

Mode opératoire

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