4-Toluenesulfonyl chloride → 1-(3-Nitro-5-(trifluoromethyl)phenyl)ethyl 4-methylbenzenesulfonate

HRID 2200142Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2200142
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[N+:12]([C:15]1[CH:16]=[C:17]([CH:25]([OH:27])[CH3:26])[CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1)([O-:14])=[O:13].C(N(CC)CC)C>ClCCl>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([O:27][CH:25]([C:17]2[CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=2)[CH3:26])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 90020647HCID 90020647, Verbindung

Produkt 1

HCID 900212721-(3-Nitro-5-(trifluoromethyl)phenyl)ethyl 4-methylbenzenesulfonateAusbeute 80,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Add p-toluenesulfonyl chloride (1.7 g, 8.9 mmol) dropwise at 0° C. to the mixture of 1-(3-nitro-5-(trifluoromethyl)phenyl)ethanol (520 mg, 2.23 mmol) and triethylamine (1.4 g, 13.4 mmol) in dichloromethane (20 mL), stir the resulting mixture for 12 hrs at ambient temperature. Concentrate the mixture under reduced pressure to get a residue, purify the residue by chromatography (silica gel, EtOAc:PE=1:10) to afford the title compound (700 mg, 80.6%).

Aufarbeitung

  1. concentrationConcentrate the mixture under reduced pressure
  2. customto get a residue
  3. custompurify the residue by chromatography (silica gel, EtOAc:PE=1:10)

Quellen und Nachweise

ORD-Eintrag
ord-5b1a1e6a98ea45049fbf43d95f007627
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359338B2

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