Methyl trifluoroacetate → 2,2,2-Trifluoro-1-(4-vinylphenyl)ethanone

HRID 1007057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1007057
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([Mg]Br)=[CH:5][CH:4]=1)=[CH2:2].[F:11][C:12]([F:18])([F:17])[C:13](OC)=[O:14]>C1COCC1>[F:11][C:12]([F:18])([F:17])[C:13]([C:6]1[CH:7]=[CH:8][C:3]([CH:1]=[CH2:2])=[CH:4][CH:5]=1)=[O:14]

Komponenten

4

Edukt 2

HCID 9893Methyl trifluoroacetateHCID 178436500HCID 178436500, Verbindung

Produkt 1

HCID 225064842,2,2-Trifluoro-1-(4-vinylphenyl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The (4-vinylphenyl)magnesium bromide solution of Example 1 was cooled to −78° C. using a dry ice /acetone bath and a solution of methyl trifluoroacetate (20.00 g, 156.19 mmol) in THF (25 mL) was added dropwise over 15 min. The reaction mixture was stirred in the cooling bath for 1 h, then quenched by pouring into cold 1N H2SO4. The aqueous solution was extracted with ether and the combined extracts were washed with brine, dried (Na2SO4), and concentrated to provide 17.81 g of a pale yellow oil. This material was purified by vacuum distillation to provide 12.65 g (46%) of a colorless oil: bp 59-60° C. (1.4 mm); 1H NMR (CDCl3) δ 8.05 (d, 2ArH), 7.55 (d, 2ArH), 6.79 (dd, CH═), 5.97 (dd, ═CHH), 5.51 (dd ═CHH).

Aufarbeitung

  1. customquenched
  2. additionby pouring into cold 1N H2SO4
  3. extractionThe aqueous solution was extracted with ether
  4. washthe combined extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ef1ea5b612c84277aee5f10c28418cd1
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06794109B2

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