Trifluoroborane Hydrofluoride → HCID 18956601, Verbindung

HRID 918128Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 918128
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[C:6](N)[CH:5]=1)(=[O:3])[CH3:2].B(F)(F)[F:20].F.N([O-])=O.[Na+]>O1CCCC1.O>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[C:6]([F:20])[CH:5]=1)(=[O:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 9855450Trifluoroborane HydrofluorideHCID 18956594HCID 18956594, VerbindungHCID 23668193Sodium Nitrite

Produkt 1

HCID 18956601HCID 18956601, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a stirred solution of intermediate B (8.8 g.) in a mixture of tetrahydrofuran (28 ml.), water (9.5 ml.) and hydrofluoroboric acid (38.5 ml. of 42% w/v acid) was slowly added a solution of sodium nitrite (2.7 g.) in water (4.5 ml.) whilst maintaining the temperature of the reaction mixture below 5°C. The mixture was then stirred for a further period of 20 minutes at 0° - 5°C. The resulting diazonium fluoroborate was collected by filtration, washed with hydrofluoroboric acid (20 ml. of 10% w/v acid) and then with methanol/ether (60 ml. of 10% methanol in ether), and finally dried in vacuo. This product was suspended in xylene (85 ml.) and the suspension heated to 70°C. at which point decomposition took place. When the reaction had subsided the mixture was refluxed for 45 minutes, after which the xylene was removed by distillation in vacuo. The residue was extracted with hot benzene. The resulting extract was cooled, washed with dilute aqueous sodium carbonate and then water, dried over anhydrous sodium carbonate, and evaporated. The residue was distilled in vacuo to give a product, b.p. 146° - 156°C./0.2 mm. which solidified on cooling. This product was recrystallized from ethanol to give 4-acetyl-2-fluoro-4'-methoxybiphenyl, m.p. 103° - 106°C. (novel intermediate C).

Aufarbeitung

  1. temperaturewhilst maintaining the temperature of the reaction mixture below 5°C
  2. filtrationThe resulting diazonium fluoroborate was collected by filtration
  3. washwashed with hydrofluoroboric acid (20 ml. of 10% w/v acid)
  4. dry with materialwith methanol/ether (60 ml. of 10% methanol in ether), and finally dried in vacuo
  5. temperaturewas refluxed for 45 minutes
  6. customafter which the xylene was removed by distillation in vacuo
  7. extractionThe residue was extracted with hot benzene
  8. extractionThe resulting extract
  9. temperaturewas cooled
  10. washwashed with dilute aqueous sodium carbonate
  11. dry with materialwater, dried over anhydrous sodium carbonate
  12. customevaporated
  13. distillationThe residue was distilled in vacuo
  14. customto give a product, b.p. 146° - 156°C./0.2 mm
  15. temperatureon cooling
  16. customThis product was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-cd541c820ae249a390c279f7c9929e67
Quelldatensatz
uspto-grants-1976_07
Patentnummer
US03969402

Notizen zur Reaktion

Wird geladen…