Trifluoroacetic acid → HCID 68502963, Verbindung

HRID 1516876Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1516876
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[O:17]C(=O)C.F[C:22](F)(F)[C:23](O)=O.CO[CH2:30][N:31]([Si](C)(C)C)C>C1(C)C=CC=CC=1>[CH3:30][N:31]1[CH2:23][CH2:22][C@@H:9]([C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[OH:17])[C@@H:8]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 44139027Phenol, 2-[(1E)-2-(2-bromophenyl)ethenyl]-4-chloro-, 1-acetateHCID 86617526HCID 86617526, Verbindung

Produkt 1

HCID 68502963HCID 68502963, VerbindungAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

trans-2-Bromo-2′-acetoxy-5′-chlorostilbene (26 g, 73 mmol) was slurried in toluene (91 ml) at 33° C. Trifluoroacetic acid (200 microliters) was added. The N-methoxymethyl-N-trimethylsilyl-N-methylamine (14.5 g; 89.7 mmol) was added to the reaction mixture over 90 minutes. After addition, the reaction was washed with water (25 ml). The toluene was removed by vacuum distillation. Ethanol (30 ml) was added and removed under reduced pressure. The oil was dissolved in methanol (90 ml). Potassium hydroxide (5 grams in 25 ml water)) was added. The product began to precipitate immediately. After 30 minutes, the pH was adjusted to 8-9 with 3N HCl (8 ml). Added water (10 ml) and cooled to less than 10° C. Filtered and washed with 1:1 methanol:water. Dried in vacuum to 26.0 grams (96% yield). Purity according to HPLC is 98% a/a.

Aufarbeitung

  1. additionAfter addition
  2. washthe reaction was washed with water (25 ml)
  3. customThe toluene was removed by vacuum distillation
  4. additionEthanol (30 ml) was added
  5. customremoved under reduced pressure
  6. dissolutionThe oil was dissolved in methanol (90 ml)
  7. additionPotassium hydroxide (5 grams in 25 ml water)) was added
  8. customto precipitate immediately
  9. temperatureAdded water (10 ml) and cooled to less than 10° C
  10. filtrationFiltered
  11. washwashed with 1:1 methanol
  12. customDried in vacuum to 26.0 grams (96% yield)

Quellen und Nachweise

ORD-Eintrag
ord-3d99283f6d3145a78ff65089fe166c30
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08227623B2

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