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

HRID 1746052Notes

Reaction equation

[F:1][C:2]1([F:15])[O:6][C:5]2[CH:7]=[C:8]([N+:12]([O-:14])=[O:13])[C:9](F)=[CH:10][C:4]=2[O:3]1.C[O-].[Na+].C[O-].[C:21](O)(=[O:23])C>CO>[F:1][C:2]1([F:15])[O:6][C:5]2[CH:7]=[C:8]([N+:12]([O-:14])=[O:13])[C:9]([O:23][CH3:21])=[CH:10][C:4]=2[O:3]1

Participants

Conditions

Temperature: 20 °C

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.

Workup

customthe volatiles were removed by rotary evaporation
washwashed with saturated NaHCO3 (10 mL), saturated NaCl (10 mL)
dry with materialdried (Na2SO4)
customevaporated
customThe material was purified by chromatography on silica with a 0-30% ethyl acetate-hexane gradient

Sources & evidence

ORD record: ord-ced94af8c2b14187a517a5cd2b9b1adf
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09149038B2

Reaction notes

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