Sulfuric Acid → 1-Bromo-2-[2-chloro-4-(methylsulphenyl)phenyl]acetylene

HRID 21458

Reaktionsgleichung

Reaktionsgleichung von HRID 21458
[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[Br:13][C:14](Br)=[CH:15][C:16]1[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][C:17]=1[Cl:24].S(=O)(=O)(O)O>CO.C1(C)C=CC=CC=1>[Br:13][C:14]#[C:15][C:16]1[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][C:17]=1[Cl:24]

Komponenten

6

Edukt 3

HCID 1118Sulfuric AcidHCID 66854Benzyltrimethylammonium hydroxideHCID 199317831,1-Dibromo-2-[2-chloro-4-(methylsulphenyl)phenyl]ethene

Produkt 1

HCID 199317681-Bromo-2-[2-chloro-4-(methylsulphenyl)phenyl]acetyleneAusbeute 12.381,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A suspension of Triton B (Reg Trade Mark, N-benzyltrimethylammonium hydroxide, 40% in methanol, 1.8 g) in toluene was added to a solution of 1,1-dibromo-2-[2-chloro-4-(methylsulphenyl)phenyl]ethene (0.96 g) in toluene. The mixture was stirred for 15 minutes. Sulphuric acid (2 m) was added and the resulting layers were separated. The organic layer was washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromotography eluted with a mixture of hexane and dichloromethane to give 1-bromo-2-[2-chloro-4-(methylsulphenyl)phenyl]acetylene 90.78 g) as a yellow oil, NMR (CDCl3) 2.5 (s,3H), 7.05(d,1H), 7.2(s,1H), 7.35(d,1H).

Aufarbeitung

  1. customthe resulting layers were separated
  2. washThe organic layer was washed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by chromotography
  7. washeluted with a mixture of hexane and dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-f5d5be1f25384852af0050db91e2a0fa
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424276

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