Reaction #1833234

Reaction equation

sodium methoxide

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

methoxide

acetic acid

→

title compound

Yield 70.0%

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

Yield 70.0%

Solvents

methanol

Conditions

Workup

1. 1
   Otherthe volatiles were removed by rotary evaporation
2. 2
   Washwashed with saturated NaHCO3 (10 mL), saturated NaCl (10 mL)
3. 3
   Dryingdried (Na2SO4)
4. 4
   Otherevaporated
5. 5
   OtherThe material was purified by chromatography on silica with a 0-30% ethyl acetate-hexane gradient

Procedure

2,2,5-Trifluoro-6-nitrobenzo[d][1,3]dioxole (2.5 g, 11 mmol) was dissolved in dry methanol (20 mL), treated with 30% sodium methoxide solution (3.1 g, 17 mmol), and stirred at 20° C. for 1 h. After excess methoxide was neutralized by addition of acetic acid, the volatiles were removed by rotary evaporation. The residue was taken up in ethyl acetate (50 mL), washed with saturated NaHCO3 (10 mL), saturated NaCl (10 mL), dried (Na2SO4) and evaporated. The material was purified by chromatography on silica with a 0-30% ethyl acetate-hexane gradient to give the title compound as a white solid (1.8 g, 70%): mp 84-85° C. 1H NMR (400 MHz, CDCl3) δ 7.71 (s, 1H), 6.89 (s, 1H), 3.98 (s, 3H); 19F NMR (376 MHz, CDCl3) δ −49.90 (s); EIMS m/z 233.

Source