Nitric Acid → Methyl 5-chloro-2-nitrobenzeneacetate

HRID 354062

Reaktionsgleichung

Reaktionsgleichung von HRID 354062
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1.S(=O)(=O)(O)O.[N+:18]([O-:21])([OH:20])=[O:19]>>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:18]([O-:20])=[O:19])=[C:7]([Cl:11])[CH:6]=1.[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:6]=[C:7]([Cl:11])[CH:8]=[CH:9][C:10]=1[N+:18]([O-:21])=[O:19]

Komponenten

5

Edukt 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 2733544Methyl 2-(3-chlorophenyl)acetate

Produkt 2

HCID 10376538Methyl 3-chloro-4-nitrophenylacetateAusbeute 33 %HCID 13265167Methyl 5-chloro-2-nitrobenzeneacetateAusbeute 51 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of (3-chloro-phenyl)acetic acid methyl ester (5.0 g, 27.1 mmol, commercially available) in concentrated sulfuric acid (7.5 mL, 140.7 mmol) at 0° C. was added drop-wise nitric acid (2.52 g, 70%, 28.0 mmol). After stirring at 0° C. for two hrs, the reaction mixture was poured into ice water and was extracted into dichioromethane. The organic extract was washed with brine, dried (anhydrous sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography over silica gel eluting with 6% ethyl acetate in hexane to give the desired (3-chloro-4-nitro-phenyl)acetic acid methyl ester as an oil (2.1 g,33%), and (5chloro-2-nitro-phenyl)acetic acid methyl ester as an oil (3.2 g, 51%). 1H NMR (CDCl3) δ: 3.69 (s, 2H), 3.74 (s, 3H), 7.33 (dd, 1H, J=8.4 Hz, 1.9 Hz), 7.50 (d, 1H, J=1.8 Hz), 7.87 (d, 1H, J=8.4 Hz.

Aufarbeitung

  1. extractionwas extracted into dichioromethane
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried (anhydrous sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography over silica gel eluting with 6% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-823a3f459fa449e384e68d514017d78a
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756395B2

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