Dichloromethane → HCID 14043449, Verbindung

HRID 1199860

Reaktionsgleichung

Reaktionsgleichung von HRID 1199860
[F:1][C:2]([F:7])=[C:3]([F:6])[CH:4]=[CH2:5].[C:8]1([S:14]Cl)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl:16]CCl>C(=O)([O-])[O-].[Ca+2]>[Cl:16][CH:4]([CH2:5][S:14][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([F:6])=[C:2]([F:7])[F:1]

Komponenten

5

Edukt 3

HCID 6344Dichloromethane2×HCID 109645Alkenes, C4-20 alpha-, gamma-omega-perfluoroHCID 11008040Benzenesulfenyl chloride

Produkt 1

HCID 14043449HCID 14043449, VerbindungAusbeute 97,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10112Calcium CarbonateKatalysator

Versuchsvorschrift

To a solution of 1,1,2-trifluoro-1,3-butadiene (8.0 g. 74 mmol) and calcium carbonate (50 mg) in 85 mL of dichloromethane at -40° C. in a round-bottom 250 mL flask was added a solution of phenylsulfenyl chloride (7.1 g, 49 mmol) in 20 mL of dichloromethane over 2 hours. The reaction mixture was left to stand overnight at room temperature and poured into ice water. The organic layer was washed with aqueous 5% sodium metabisulfite solution and brine, then dried over anhydrous magnesium sulfate. Evaporation of solvent followed by distillation gave 12.1 g (97.5%) of 3-chloro-4-phenylthio-1,1,2-trifluoro-1-butene as a light yellow oil, bp 84°-86° C. (1.0 mm Hg). 1H-NMR (300 MHz, CDCl3): δ 3.39(2H, d, J=8 Hz), 4.58(1H, ttd, J=1.5, 8, 33 Hz), 7.2-7.4(5H, phenyl protons). Mass spectrum: m/e=252,254 (M+). 19F-NMR (300 MHz, CDCl3): φ F3 =-11.8, F2 =116.7, F1 =99.3. J(F12 =64.5, J(F23)=111.2, J(F13)=33.0, J(F3H)=26.4.

Aufarbeitung

  1. waitThe reaction mixture was left
  2. washThe organic layer was washed with aqueous 5% sodium metabisulfite solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customEvaporation of solvent
  5. distillationfollowed by distillation

Quellen und Nachweise

ORD-Eintrag
ord-abfc180c428e46f59b74498849c432e8
Quelldatensatz
uspto-grants-1990_02
Patentnummer
US04902835

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