Dimethylformamide → 4-Bromo-3-(difluoromethoxy)nitrobenzene

HRID 491621

Reaktionsgleichung

Reaktionsgleichung von HRID 491621
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].Cl[C:13]([F:20])([F:19])C(OCC)=O.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH:13]([F:20])[F:19]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 67843Acetic acid, 2-chloro-2,2-difluoro-, ethyl esterHCID 128671362-Bromo-5-nitrophenol

Produkt 1

HCID 534159044-Bromo-3-(difluoromethoxy)nitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a N2 purged round bottom flask was added 2-bromo-5-nitrophenol (29.0 g, 133 mmol, 1.0 eq.) followed by 16.8 mL (133 mmol, 1.0 eq) of ethyl chlorodifluoroacetate and 18.8 g of K2CO3 (133 mmol, 1.0 eq.). Anhydrous DMF (300 mL) was added and the mixture was stirred at 70° C. for 5 h. The mixture was cooled to RT and the solvent was removed. The obtained crude mixture was dissolved in CH2Cl2 (500 mL) and washed with 1 N NaOH (aq.). The organic layer was dried (MgSO4), filtered and evaporated. The crude material was further purified by column chromatography (0-5% EtOAc in hexanes) providing pure 1-bromo-2-difluoromethoxy-4-nitro-benzene.

Aufarbeitung

  1. temperatureThe mixture was cooled to RT
  2. customthe solvent was removed
  3. customThe obtained crude mixture
  4. washwashed with 1 N NaOH (aq.)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude material was further purified by column chromatography (0-5% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a1dbb3c8f81b4fd0b726c1b5c355fe7c
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531553B2

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