Hydrochloric Acid → 1-Trifluoromethyl2,4,6-trinitrobenzene

HRID 981405Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 981405
[F:1][C:2]([F:7])([F:6])[C:3]([O-])=O.[K+].[N+:9]([C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])C=[C:14]([N+:21]([O-:23])=[O:22])[CH:13]=1)([O-:11])=[O:10].C(OCl)(C)(C)C.Cl>CN(C)C=O.CS(C)=O>[F:1][C:2]([F:7])([F:6])[C:3]1[C:16]([N+:18]([O-:20])=[O:19])=[CH:17][C:12]([N+:9]([O-:11])=[O:10])=[CH:13][C:14]=1[N+:21]([O-:23])=[O:22]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 74341,3,5-TrinitrobenzeneHCID 521297Tert-Butyl hypochloriteHCID 23662811Potassium trifluoroacetate

Produkt 1

HCID 117809461-Trifluoromethyl2,4,6-trinitrobenzeneAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A mixture of potassium trifluoroacetate (210 mg, 1.4 mmol and 1,3,5-trinitrobenzene (100 mg, 0.47 mmol) in one mL of N,N-dimethylformamide (DMF) or in one mL of dimethylsulfoxide (DMSO) was heated at 150° C. for one hour. A deep red solution of a Meisenheimer complex of formula (II) above (Z=nitro; Q=trifluoromethyl; R and R'=H; M=K; and n=1) was obtained. The structure of the complex was verified by NMR spectroscopy. Oxidation of a DMF solution of this complex by dropwise addition of tert-butylhypochlorite until the red color disappeared (about seven drops) followed by aqueous workup (10 mL of 1M HCl, extracted with three portions of diethyl ether afforded an oil. This was purified by preparative thin layer chromatography (one 2 mm silica gel plate eluted with 50% petroleum ether/50% dichloromethane) to give 53 mg (40% yield) of 1-trifluoromethyl2,4,6-trinitrobenzene.

Aufarbeitung

  1. customand n=1) was obtained
  2. extractionextracted with three portions of diethyl ether
  3. customafforded an oil
  4. customThis was purified by preparative thin layer chromatography (one 2 mm silica gel plate eluted with 50% petroleum ether/50% dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-773f3854f4e7459a94d45244a025c257
Quelldatensatz
uspto-grants-1991_02
Patentnummer
US04990699

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