Catechol → 4-Fluoro-2H-1,3-benzodioxole

HRID 495024

Reaktionsgleichung

Reaktionsgleichung von HRID 495024
BrCBr.[F:4][C:5]1[CH:11]=[CH:10][CH:9]=[C:7]([OH:8])[C:6]=1[OH:12].[C:13]1(C(=CC=CC=1)O)O>[Cl-].C[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC.[OH-].[Na+].C(Cl)Cl.O>[F:4][C:5]1[CH:11]=[CH:10][CH:9]=[C:7]2[O:8][CH2:13][O:12][C:6]=12

Komponenten

8

Edukt 3

HCID 289CatecholHCID 3024DibromomethaneHCID 677643-Fluorocatechol

Produkt 1

HCID 157672604-Fluoro-2H-1,3-benzodioxole

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 21218Trioctylmethylammonium chlorideKatalysatorHCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

Alliquat 336 (methyltrioctylammonium chloride (0.63 g, 0.0016 mol), dibromomethane (40.7 g, 234.2 mmol), and water (31 mL) were placed in a 500 mL 3-necked flask equipped with an addition funnel, condenser and a stir bar. The addition funnel was charged with a solution of 3-fluorocatechol (20.0 g, 6.1 mmol) in 5M sodium hydroxide (80 mL). The mixture in the flask was heated to reflux and the solution of the catechol was added dropwise with good stirring over 1.5 hours. The resulting dark mixture was heated an additional 2 hours at reflux. After cooling to room temperature, the reaction was diluted with methylene chloride and water. The aqueous layer was extracted with methylene chloride and the combined organic layers were dried and concentrated to give 1-fluoro-2,3-methylenedioxybenzene (14.6 g, 104.2 mmol) as a dark yellow oil: 1H NMR (CDCl3): δ 6.80 (m, 1H), 6.68 (m, 2H), 6.04 (s, 2H).

Aufarbeitung

  1. customequipped with an addition funnel, condenser and a stir bar
  2. temperatureThe mixture in the flask was heated
  3. temperatureto reflux
  4. temperatureThe resulting dark mixture was heated an additional 2 hours
  5. temperatureat reflux
  6. extractionThe aqueous layer was extracted with methylene chloride
  7. customthe combined organic layers were dried
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3eb7de94d4b447aca1624806392c413c
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538214B2

Verknüpfte Notizen

Wird geladen…