Hydrochloric Acid → 1-(2-Chloro-4-fluoro-5-nitrophenyl)ethanone

HRID 428396Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 428396
[Cl-].C[Zn+].[Cl:4][C:5]1[CH:13]=[C:12]([F:14])[C:11]([N+:15]([O-:17])=[O:16])=[CH:10][C:6]=1[C:7](Cl)=[O:8].Cl.[CH2:19](Cl)Cl>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:4][C:5]1[CH:13]=[C:12]([F:14])[C:11]([N+:15]([O-:17])=[O:16])=[CH:10][C:6]=1[C:7](=[O:8])[CH3:19]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 151243842-Chloro-4-fluoro-5-nitrobenzoyl chlorideHCID 178477797HCID 178477797, Verbindung

Produkt 1

HCID 183144841-(2-Chloro-4-fluoro-5-nitrophenyl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A 2 M solution of methylzinc chloride in tetrahydrofuran (5.00 mL, 10.1 mmol) is treated dropwise with a solution of 2-chloro-4-fluoro-5-nitrobenzoyl chloride (2.00 g, 8.40 mmol) in tetrahydrofuran, treated with tetrakis(triphenylphosphine)palladium(0) (0.400 g, 0.350 mmol), stirred at room temperature for one hour, and poured into 3 N hydrochloric acid. The resultant aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water and saturated sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a dark liquid. Flash column chromatography of the liquid using silica gel and a methylene chloride in hexanes solution (6:4) gives the title product as an off-white solid (mp 66-68° C.) which is identified by NMR spectral analyses.

Aufarbeitung

  1. extractionThe resultant aqueous mixture is extracted with ethyl acetate
  2. washwashed sequentially with water and saturated sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a dark liquid

Quellen und Nachweise

ORD-Eintrag
ord-02ccbd9d04344c99a070d7381af9846a
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313295B1

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