1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 1-(3-tert-butoxy-4-nitrophenyl)-3,4-difluoro-1H-pyrrole

HRID 1528054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1528054
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:3]=1.Cl.[F:17][C:18]1(F)[C:22](F)([F:23])[CH2:21][NH:20][CH2:19]1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC(C)([O-])C.[Na+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[C:12]([O:11][C:4]1[CH:3]=[C:2]([N:20]2[CH:21]=[C:22]([F:23])[C:18]([F:17])=[CH:19]2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9])([CH3:15])([CH3:14])[CH3:13]

Komponenten

8

Edukt 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 226459203,3,4,4-Tetrafluoropyrrolidine HydrochlorideHCID 23676156Sodium t-butoxideHCID 467394974-Bromo-2-tert-butoxy-1-nitrobenzene

Produkt 1

HCID 712721661-(3-tert-butoxy-4-nitrophenyl)-3,4-difluoro-1H-pyrroleAusbeute 56,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A suspension of 4-bromo-2-(tert-butoxy)-1-nitrobenzene (13.7 g), 3,3,4,4-tetrafluoropyrrolidine hydrochloride (9.87 g), Pd2(dba)3 (0.916 g), Xantphos (2.31 g) and sodium tert-butoxide (19.2 g) in 1,4-dioxane (150 mL) was stirred at 90° C. for 4 hr under an argon atmosphere. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate), and recrystallized from hexane/ethyl acetate to give the title compound (8.35 g).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)
  6. customrecrystallized from hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ea487da9764f444eb70e0f1476b861fb
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090586B2

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