Nitric Acid → 2-Fluoro-4-nitroanisole

HRID 1388562

Reaktionsgleichung

Reaktionsgleichung von HRID 1388562
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[N+:10]([O-])([OH:12])=[O:11].O>C(OC(=O)C)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=[CH:4][C:3]=1[O:8][CH3:9]

Komponenten

5

Edukt 3

HCID 944Nitric AcidHCID 962WaterHCID 675762-Fluoroanisole

Produkt 1

HCID 2231042-Fluoro-4-nitroanisole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

To a cold (-2°), stirred solution of 285 g. (2.26 mol) of 2-fluoroanisole in 1.1 L of acetic anhydride was added, dropwise, 114 mL of fuming nitric acid (sp. gr. 1.59) at such a rate that the reaction temperature remained between -2° and 0°. The reaction mixture was stirred for 5 hours at this temperature then poured into 4.0 L of water. The suspension was stirred for 1.5 hours, stored for 15 hours, then extracted with methylene chloride (2×1.0 L). The combined extracts were washed with water (2×500 mL), dried over anhydrous magnesium sulfate, then concentrated in vacuo (475 g.). Crystallization from ethanol gave 147.4 g. (38%) of material suitable for further transformation. Additional material (34.5 g.) was obtained from three scouting runs.

Aufarbeitung

  1. customremained between -2° and 0°
  2. stirringThe reaction mixture was stirred for 5 hours at this temperature
  3. stirringThe suspension was stirred for 1.5 hours
  4. extractionextracted with methylene chloride (2×1.0 L)
  5. washThe combined extracts were washed with water (2×500 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo (475 g.)
  8. customCrystallization from ethanol
  9. customgave 147.4 g
  10. customAdditional material (34.5 g.) was obtained from three scouting runs

Quellen und Nachweise

ORD-Eintrag
ord-0d470ade0b5040ffb2393d61c940a761
Quelldatensatz
uspto-grants-1984_02
Patentnummer
US04431807

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