1-Bromo-4-iodobenzene → Ethyl (4-bromophenyl)(difluoro)acetate

HRID 2405159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2405159
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[CH2:9]([O:11][C:12](=[O:17])[C:13](Br)([F:15])[F:14])[CH3:10]>[Cu].CS(C)=O>[CH2:9]([O:11][C:12](=[O:17])[C:13]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)([F:15])[F:14])[CH3:10]

Komponenten

5

Edukt 2

HCID 115221-Bromo-4-iodobenzeneHCID 69585Ethyl bromodifluoroacetate2×

Produkt 1

HCID 46220010Ethyl (4-bromophenyl)(difluoro)acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

According to the Kumadaki method (supra) and the above-described scheme, 4-bromoiodobenzene (848.7 mg, 3.0 mmol), bromodifluoroacetic acid ethyl ester (Compound 1f; 608.9 mg, 3.0 mmol), copper powder (381 mg, 6.0 mmol) and DMSO (6.0 mL) were put into a two-neck reaction tube, and the mixture was stirred under argon atmosphere at 55° C. for 24 hours. The reaction mixture was extracted with ethyl acetate and washed with water, and an organic layer was dried with anhydrous sodium sulfate. Ethyl acetate was distilled away under reduced pressure, and by carrying out purification by silica gel column chromatography, 2-(4-bromophenyl)-2,2-difluoroacetic acid ethyl ester (Compound 2f) was obtained with a yield of 69%.

Aufarbeitung

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialan organic layer was dried with anhydrous sodium sulfate
  4. distillationEthyl acetate was distilled away under reduced pressure
  5. custompurification by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cb8277a80ab741ecb27378b02c15de61
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802886B2

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