Propiolic Acid → 4-Bromo-3,5-dimethylphenyl propiolate

HRID 1483185Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1483185
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[C:11](O)(=[O:14])[C:12]#[CH:13].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:11]([O:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([Br:1])=[C:3]([CH3:10])[CH:4]=1)(=[O:14])[C:12]#[CH:13]

Komponenten

6

Edukt 3

HCID 10110Propiolic AcidHCID 10868DicyclohexylcarbodiimideHCID 819704-Bromo-3,5-dimethylphenol

Produkt 1

HCID 725452334-Bromo-3,5-dimethylphenyl propiolateAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 4-bromo-3,5-dimethylphenol (40.87 g, 203.3 mmol) and propiolic acid (20.91 g, 298.5 mmol) in CH2Cl2 (400 mL) was added DCC (50.78 g, 246.1 mmol) in CH2Cl2 (100 mL) and DMAP (0.82 g, 6.7 mmol) at 0° C. The mixture was stirred at room temperature for 3 h and filtered. The filtrate was concentrated and purified by silica gel column chromatography (hexanes:EtOAc:CH2Cl2=20:1:10). The fractions containing the desired compound were concentrated. To the concentrate added hexane and the precipitated solid was collected by filtration. The solid was washed with hexane and dried to give the title compound 6-1 (26.12 g, 51% yield) as a white solid.

Aufarbeitung

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. custompurified by silica gel column chromatography (hexanes:EtOAc:CH2Cl2=20:1:10)
  4. additionThe fractions containing the desired compound
  5. concentrationwere concentrated
  6. additionTo the concentrate added hexane
  7. filtrationthe precipitated solid was collected by filtration
  8. washThe solid was washed with hexane
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-53954c35f7804a46a5de309dfd918267
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09416121B2

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