Nitric Acid → 1-(2-Chloroethoxy)-2,6-dibromo-4-fluoro-3-nitrobenzene

HRID 399011Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 399011
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[C:10]([Br:11])=[CH:9][C:8]([F:12])=[CH:7][C:6]=1[Br:13].[N+:14]([O-])([OH:16])=[O:15]>S(=O)(=O)(O)O>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[C:6]([Br:13])=[CH:7][C:8]([F:12])=[C:9]([N+:14]([O-:16])=[O:15])[C:10]=1[Br:11]

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 108304061,3-Dibromo-2-(2-chloroethoxy)-5-fluorobenzene

Produkt 1

HCID 105716291-(2-Chloroethoxy)-2,6-dibromo-4-fluoro-3-nitrobenzeneAusbeute 97,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel2×

Versuchsvorschrift

To a solution of 1-(2-chloroethoxy)-2,6-dibromo-4-fluorobenzene (65.8 g, 0.20 mol) in concentrated sulfuric acid (165 mL) maintained at room temperature using a water bath was slowly added a solution of nitric acid in sulfuric acid (10 mL HNO3 in 165 mL H2SO4). The reaction was allowed to stir at room temperature for 1 hour then poured into ice (1.5 L) and extracted with methylene chloride (2×300 mL). The combined organic layers were washed with aqueous sodium bicarbonate (150 mL) and dried over anhydrous magnesium sulfate, filtered, and the solvent removed under vacuum to afford 73.3 g (97.1%) a white crystalline solid: mp 56°-57° C.; MS EI m/e 375/377/379/381; 1H NMR (CDCl3) δ 3.91 (2H, t, J=5.9 Hz), 4.29 (2H, d, J=5.9 Hz), 7.54 (8.1 Hz).

Aufarbeitung

  1. extractionextracted with methylene chloride (2×300 mL)
  2. washThe combined organic layers were washed with aqueous sodium bicarbonate (150 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f4cc063603cd42ef8ef096db1305ef14
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05817690

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