Hydrochloric Acid → HCID 22312920, Verbindung

HRID 351561Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 351561
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[Cl:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[C:18]([Cl:25])[C:17]=1Cl.Cl>C1COCC1.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.[OH-].[Na+]>[Cl:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[C:18]([Cl:25])[C:17]=1[CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:11]([F:12])([F:13])[F:14])[CH:4]=1)[C:9]#[N:10]

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 883653,4,5-TrichloronitrobenzeneHCID 50046852-(4-Chloro-3-(trifluoromethyl)phenyl)acetonitrile

Produkt 1

HCID 22312920HCID 22312920, VerbindungAusbeute 86,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A solution of 4-chloro-3-(trifluoromethyl)benzeneacetonitrile (0.114 mol) in THF (100 ml) was added dropwise at RT to a solution of 1,2,3-trichloro-5-nitrobenzene (0.114 mol) and N,N,N-triethylbenzenemethanaminium chloride (3 g) in NaOH (150 ml) and THF (100 ml). The mixture was stirred at RT for 2 hours, then poured out on ice, acidified with a concentrated HCl solution and extracted with CH2Cl2. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was crystallized from DIPE. The precipitate was filtered off and dried, yielding 40.4 g (86.5%) of (±)-2,6-dichloro-α-[4-chloro-3-(trifluoromethyl)phenyl]-4-nitrobenzene-acetonitrile (interm. 1).

Aufarbeitung

  1. additionpoured out on ice
  2. extractionextracted with CH2Cl2
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was crystallized from DIPE
  8. filtrationThe precipitate was filtered off
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e8a55f610be642cca1f13c923bd4dd99
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743792B2

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