Nitric Acid → Dimethyl 2-fluoro-5-nitrobenzene-1,4-dicarboxylate

HRID 970325

Reaktionsgleichung

[F:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[N+:16]([O-])([OH:18])=[O:17]>S(=O)(=O)(O)O>[CH3:7][O:6][C:4](=[O:5])[C:3]1[CH:8]=[C:9]([N+:16]([O-:18])=[O:17])[C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:11][C:2]=1[F:1]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a mixture of dimethyl 2-fluoroterephthalate (42.0 g, 0.198 mol) in concentrated sulfuric acid (200 mL) at 0° C. was added 36 mL of a 1:1 mixture of nitric acid and sulfuric acid dropwise. The mixture was stirred at 0° C. for 15 min., the ice-bath was removed, and the reaction mixture was stirred for an additional 45 min. HPLC indicated that the starting material had been consumed. The reaction mixture was poured over ice and extracted with EtOAc. The organic layer was collected, washed with brine, and dried over anhydrous sodium sulfate. Concentration under reduced pressure followed by recrystallization from MeOH afforded 48.5 g (95%) of 174A as a white solid. HPLC retention time=2.69 min. (Condition B). 1H-NMR (500 MHz, CDCl3) δ 3.95 (s, 3H), 3.98 (s, 3H), 7.44 (d, 1H), and 8.59 (d, 1H).

Aufarbeitung

additionwas added
customthe ice-bath was removed
stirringthe reaction mixture was stirred for an additional 45 min
customhad been consumed
additionThe reaction mixture was poured over ice
extractionextracted with EtOAc
customThe organic layer was collected
washwashed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationConcentration under reduced pressure
customfollowed by recrystallization from MeOH

Quellen und Nachweise

ORD-Eintrag: ord-ce1f9cee4e154e1297f5a4a21eed9698
Quelldatensatz: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07312209B2

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