Hexane → 1,1-Dibromo-2-[2-chloro-4-(methylsulphenyl)phenyl]ethene

HRID 2380206Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2380206
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)[Br:21].[Cl:25][C:26]1[CH2:33][C:32](=[S:34])[CH:31]=[CH:30][C:27]=1[CH:28]=O.CCCCCC>ClCCl>[Br:21][C:20]([Br:24])=[CH:28][C:27]1[CH:30]=[CH:31][C:32]([S:34][CH3:1])=[CH:33][C:26]=1[Cl:25]

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 867482642-Chloro-4-(sulphenyl)-benzaldehyde

Produkt 1

HCID 199317831,1-Dibromo-2-[2-chloro-4-(methylsulphenyl)phenyl]etheneAusbeute 62,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Triphenyl phosphine (2.5 g) was added to a stirred solution of carbon tetrabromide (1.48 g) in dichloromethane maintaining the temperature at 0° C. The mixture was stirred for 0.5 hours and 2-chloro-4-(sulphenyl)-benzaldehyde (1.0 g) was added. The resultant mixture was stirred for 0.5 hours and poured into hexane. The resulting solid was filtered off and washed with ether. The combined filtrates were evaporated to dryness and the residue was purified by chromatrography eluted with hexane to give 1,1-dibromo-2-[2-chloro-4-(methylsulphenyl)phenyl]ethene (0.96 g) as a white solid, NMR (CDCl3) 2.45 (s,3H), 7.15(d,1H), 7.25(s,1H), 7.55(s,1H), 7.6(d,1H).

Aufarbeitung

  1. filtrationThe resulting solid was filtered off
  2. washwashed with ether
  3. customThe combined filtrates were evaporated to dryness
  4. customthe residue was purified by chromatrography
  5. washeluted with hexane

Quellen und Nachweise

ORD-Eintrag
ord-83fe531f4476447f9aae62051afdd24b
Quelldatensatz
uspto-grants-1994_11
Patentnummer
US05366957

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