Hydrochloric Acid → HCID 86639514, Verbindung

HRID 556248

Reaktionsgleichung

Reaktionsgleichung von HRID 556248
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)=[CH2:2].[OH:12][CH:13]([C:21]([F:24])([F:23])[F:22])[C:14]([F:20])([F:19])[S:15]([O-:18])(=[O:17])=[O:16].[C:25]1([S+:31]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C.Cl>C(Cl)Cl>[F:20][C:14]([F:19])([S:15]([O-:18])(=[O:17])=[O:16])[CH:13]([O:12][C:7](=[O:8])[C:6]1[CH:10]=[CH:11][C:3]([CH:1]=[CH2:2])=[CH:4][CH:5]=1)[C:21]([F:24])([F:22])[F:23].[C:38]1([S+:31]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 110520284-Vinylbenzoyl chlorideHCID 86612198HCID 86612198, Verbindung

Produkt 1

HCID 86639514HCID 86639514, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Under ice cooling, 2.0 g (12 mmol) of the resulting 4-vinylbenzoyl chloride in methylene chloride was added dropwise to a mixture of 4.9 g (10 mmol) of triphenylsulfonium 2-hydroxy-1,1,3,3,3-pentafluoropropane-1-sulfonate in Synthesis Example 1-11, 1.21 g (12 mmol) of triethylamine, 0.24 g (2 mmol) of N,N-dimethylaminopyridine, and 20 g of methylene chloride. The reaction mixture was stirred at room temperature for 2 hours. Thereafter, 11 g of 5% dilute hydrochloric acid was added. The organic layer was separated and washed with water whereupon methylene chloride was distilled off under vacuum. The residue was combined with 30 g of methyl isobutyl ketone and washed with dilute aqueous ammonia and then with water, whereupon the methyl isobutyl ketone was distilled off under vacuum. Diisopropyl ether was added to the residue, followed by decantation. The target compound, triphenylsulfonium 1,1,3,3,3-pentafluoro-2-(4-vinyl-benzoyloxy)-propane-1-sulfonate was obtained as colorless oil (5.3 g, yield 85%). The compound has the following structure.

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with water whereupon methylene chloride
  3. distillationwas distilled off under vacuum
  4. washwashed with dilute aqueous ammonia
  5. distillationwith water, whereupon the methyl isobutyl ketone was distilled off under vacuum
  6. additionDiisopropyl ether was added to the residue

Quellen und Nachweise

ORD-Eintrag
ord-0a62daba88754b8f907e8fdc4f623115
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08057985B2

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