Reaction #1833235

Reaction equation

hydrogen

2,2-Difluoro-5-methoxy-6-nitrobenzo[d][1,3]dioxole

→

title compound

Yield 101.2%

2,2-Difluoro-6-methoxybenzo[d][1,3]dioxol-5-amine

Yield 101.2%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   Otherthe catalyst was removed by filtration
2. 2
   Otherthe solvent was removed by evaporation
3. 3
   Otherthe product dried under vacuum

Procedure

2,2-Difluoro-5-methoxy-6-nitrobenzo[d][1,3]dioxole (1.7 g, 7.3 mmol) was dissolved in ethyl acetate (50 mL) and treated with 5% palladium on carbon (200 mg) and hydrogen at 40-50 pounds per square inch (psi) on a shaker. After 90 min, the catalyst was removed by filtration, the solvent was removed by evaporation, and the product dried under vacuum to give the title compound as a brown solid (1.5 g, qt (quantitative)): 1H NMR (400 MHz, CDCl3) δ 6.63 (s, 1H), 6.50 (s, 1H), 3.82 (s, 3H), 3.76 (d, J=23.0 Hz, 2H); 19F NMR (376 MHz, CDCl3) δ −50.32 (s); EIMS m/z 203.

Source