Methanol → HCID 118046800, Verbindung

HRID 63878Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 63878
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[C:20]([F:24])=[C:19]([Cl:25])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=2)=[CH:4][C:3]=1[CH3:26].[C:27]([O-:30])(=[O:29])C.[Na+].[CH3:32]O>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]>[Cl:25][C:19]1[CH:18]=[C:17]([C:11]2([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:27]([O:30][CH3:32])=[O:29])=[C:3]([CH3:26])[CH:4]=3)[CH2:12]2)[CH:22]=[C:21]([Cl:23])[C:20]=1[F:24]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 517045Sodium AcetateHCID 118046969HCID 118046969, Verbindung

Produkt 1

HCID 118046800HCID 118046800, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

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

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Into a 30-mL pressure tank reactor (20 atm), was placed methanol (10 mL), 3-(4-bromo-3-methylphenyl)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazole (80 mg, 0.17 mmol, 1.00 equiv), sodium acetate (41 mg, 0.50 mmol, 3.00 equiv), Pd(dppf)Cl2 (12 mg, 0.02 mmol, 0.10 equiv), CO (20 atm). The resulting solution was stirred overnight at 110° C. in an oil bath. The reaction mixture was cooled. The residue was purified by Prep-TLC (EtOAc:PE=10:1). This resulted in 60 mg (78%) of methyl 4-[5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylbenzoate as colorless oil.

Aufarbeitung

  1. customInto a 30-mL pressure tank reactor (20 atm), was placed
  2. temperatureThe reaction mixture was cooled
  3. customThe residue was purified by Prep-TLC (EtOAc:PE=10:1)
  4. customThis resulted in 60 mg (78%) of methyl 4-[5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylbenzoate as colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-08c948a789b84a4ba92f40f0ecfa1a4d
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447084B2

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