4-Toluenesulfonyl chloride → 1-(Chloromethyl)-3-nitro-5-(trifluoromethyl)benzene

HRID 2200183Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2200183
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:14]O)[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-:3])=[O:2].C(N(CC)CC)C.C1(C)C=CC(S([Cl:32])(=O)=O)=CC=1.CCOC(C)=O>C(Cl)Cl>[Cl:32][CH2:14][C:6]1[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Komponenten

6

Edukt 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 18621888(3-Nitro-5-(trifluoromethyl)phenyl)methanol

Produkt 1

HCID 684250951-(Chloromethyl)-3-nitro-5-(trifluoromethyl)benzeneAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Dissolve [3-nitro-5-(trifluoromethyl)phenyl]methanol (1.1 g, 5.18 mmol) and triethylamine (1.62 mL) in DCM (20 mL), cool to 0° C., add slowly p-toluenesulfonyl chloride (1.1 g, 6.02 mmol). After the addition, stir the reaction at room temperature for 15 hrs. TLC (EtOAc:PE=1:15) shows the reaction is complete. Concentrate under reduced pressure to get the crude product. Purification by chromatography (silica gel, EtOAc:PE=1:15) affords the title compound (655 mg, 55%).

Aufarbeitung

  1. additionAfter the addition
  2. customthe reaction at room temperature for 15 hrs
  3. concentrationConcentrate under reduced pressure
  4. customto get the crude product
  5. customPurification by chromatography (silica gel, EtOAc:PE=1:15)

Quellen und Nachweise

ORD-Eintrag
ord-983bd052bb7842929f7a3543e6f1959e
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359338B2

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