Nitrogen → methyl (2E)-3-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-2-propenoate

HRID 1496920

Reaktionsgleichung

Reaktionsgleichung von HRID 1496920
Br[C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[F:14][C:15]([F:31])([F:30])[O:16][C:17]1[CH:22]=[CH:21][C:20](C2C=CC(O)=CC=2)=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+].N#N>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:14][C:15]([F:30])([F:31])[O:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=2)=[CH:19][CH:18]=1

Komponenten

7

Edukt 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 816774Methyl 4-bromocinnamateHCID 120087344-(4-Trifluoromethoxyphenyl)phenol

Produkt 1

HCID 54757818methyl (2E)-3-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-2-propenoateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of methyl (E)-3-(4-bromophenyl)-2-propenoate (99) (0.500 g, 2.07 mmol) and 4-(trifluoromethoxy)phenylboronic acid (44) (0.612 g, 2.97 mmol) in dioxane (40 mL) and aqueous K2CO3 (2M, 10 mL, 20 mmol) was purged with N2. Pd(dppf)Cl2 (0.050 g, 0.06 mmol) was added and the solution was refluxed under N2 for 1 h. The dioxane was removed and the residue was extracted with EtOAc, the organic fraction was dried and the solvent was removed. Column chromatography of the residue on silica gel using gradient elution (hexanes to CH2Cl2) gave methyl (2E)-3-[4′-(trifluoromethoxy)[1,1′-biphenyl]-4-yl]-2-propenoate (100) (0.567 g, 85%) as a white solid: mp 98-100° C.; 1H NMR (CDCl3) δ 7.73 (d, J=16.0 Hz, 1H), 7.56-7.63 (m, 6H), 7.30 (dd, J=8.8, 0.9 Hz, 2H), 6.48 (d, J=16.0 Hz, 1H), 3.82 (s, 3H). APCI MS m/z 323 [M+H]+.

Aufarbeitung

  1. temperaturethe solution was refluxed under N2 for 1 h
  2. customThe dioxane was removed
  3. extractionthe residue was extracted with EtOAc
  4. customthe organic fraction was dried
  5. customthe solvent was removed
  6. washColumn chromatography of the residue on silica gel using gradient elution (hexanes to CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-af23c11d57c3404a979a89cdabf7813c
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09198913B2

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