Nitromethane → 2,2-Difluoro-5-(2-nitro-vinyl)-benzo[1,3]dioxole

HRID 2110698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2110698
[F:1][C:2]1([F:13])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]=O)=[CH:10][C:4]=2[O:3]1.[N+:14]([CH3:17])([O-:16])=[O:15].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[F:1][C:2]1([F:13])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]=[CH:17][N+:14]([O-:16])=[O:15])=[CH:10][C:4]=2[O:3]1

Komponenten

5

Edukt 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 27369732,2-Difluoro-5-formylbenzodioxole2×

Produkt 1

HCID 672340792,2-Difluoro-5-(2-nitro-vinyl)-benzo[1,3]dioxoleAusbeute 56,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 2,2-difluoro-benzo[1,3]dioxole-5-carbaldehyde [5.48 g, 29.44 mmol, Intermediate (60)] and nitromethane (4.78 mL, 88.32 mmol) in acetic acid (90 mL) is added ammonium acetate (5.67 g, 73.6 mmol). The reaction mixture is heated to reflux for 5.5 hours. Acetic acid is removed in vacuo and the residue is added water (20 mL) and extracted with DCM (3×50 mL), organic layers are combined and washed with 2 N sodium hydroxide, water and brine, dried over sodium sulfate and concentrated. The solid obtained is crystallized in methanol/DCM (1:1) to yield intermediate 2,2-difluoro-5-(2-nitro-vinyl)-benzo[1,3]dioxole [3.83 g, Intermediate (61)] as a solid.

Aufarbeitung

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 5.5 hours
  3. customAcetic acid is removed in vacuo
  4. additionthe residue is added water (20 mL)
  5. extractionextracted with DCM (3×50 mL), organic layers
  6. washwashed with 2 N sodium hydroxide, water and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe solid obtained
  10. customis crystallized in methanol/DCM (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-3f567adf30e94a97ac7a768e5d4d0fc5
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517889B2

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