Nitrogen → 2-Bromo-1-[3-nitro-4-(trifluoromethyl)phenyl]ethanone

HRID 539745

Reaktionsgleichung

Reaktionsgleichung von HRID 539745
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[C:13]([F:16])([F:15])[F:14])[C:7]([OH:9])=O)([O-:3])=[O:2].S(Cl)(Cl)=O.[CH3:21][Si](C=[N+]=[N-])(C)C.[BrH:28].CC(O)=O.N#N>C(Cl)Cl>[Br:28][CH2:21][C:7]([C:6]1[CH:10]=[CH:11][C:12]([C:13]([F:16])([F:15])[F:14])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:9]

Komponenten

7

Edukt 5

HCID 947NitrogenHCID 24386Thionyl ChlorideHCID 167693TrimethylsilyldiazomethaneHCID 27790153-Nitro-4-(trifluoromethyl)benzoic acidHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Produkt 1

HCID 575162692-Bromo-1-[3-nitro-4-(trifluoromethyl)phenyl]ethanoneAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

3-Nitro-4-(trifluoromethyl)benzoic acid (Matrix Scientific, 2.35 g, 10 mmol) is dissolved in thionyl chloride (22 mL, 300 mmol). The stirred solution is heated at 95° C. for 16 hr, then cooled, concentrated and CH2Cl2 (51 mL) and trimethylsilyldiazomethane (20 mL, 2 M in Hexanes, 40 mmol) are added and the reaction is stirred for 2 hr at room temp. The mixture is cooled to 0° C. and HBr/HOAc (6.33 mL, 33% of HBr in HOAc) is added dropwise (N2 evolution). After addition the mixture is stirred at 0° C. for 5 min, then concentrated and purified by silica gel chromatography (CH2Cl2) to give the title compound (2.59 g, 83% yield). LCMS m/z=313.5 [M+H]+, tR=2.65 min.

Aufarbeitung

  1. temperaturecooled
  2. concentrationconcentrated
  3. temperatureThe mixture is cooled to 0° C.
  4. additionAfter addition the mixture
  5. stirringis stirred at 0° C. for 5 min
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-e5755538df574e1e83fd0aea75d7ee18
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871767B2

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