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Tri-o-tolylphosphine → tert-butyl (3E)-4-(3-amino-4-phenylphenyl)-3-butenoate

HRID 1518632
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1518632
[C:1]1([C:7]2[CH:13]=[C:12](Br)[CH:11]=[CH:10][C:8]=2[NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]([O:19][C:20](=[O:24])[CH2:21][CH:22]=[CH2:23])([CH3:18])([CH3:17])[CH3:16].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(C(C)C)CC)(C)C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:9][C:8]1[CH:10]=[C:11](/[CH:23]=[CH:22]/[CH2:21][C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:24])[CH:12]=[CH:13][C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 2295504-Bromo-2-phenylanilineHCID 639778tert-Butyl 3-Butenoate

Produkt 1

HCID 66597453tert-butyl (3E)-4-(3-amino-4-phenylphenyl)-3-butenoateAusbeute 78,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845
palladium(II) acetate
Katalysator
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

2-Phenyl-4-bromoaniline (564.7 mg, 2.28 mmol) was dissolved in N,N-dimethylformamide (25 mL) and, at room temperature, thereto were added tert-butyl-3-butenoate (582.5 mg, 4.10 mmol), tri-(o-tolyl)phosphine (1.87 g, 6.16 mmol), and diisopropylethylamine (0.78 mL, 4.56 mmol). The reaction mixture was deaerated, palladium acetate (67.4 mg, 0.30 mmol) was added, and the mixture was deaerated again. After stirring at 90° C. overnight, the reaction mixture was filtered through celite and washed with ethyl acetate (120 mL). The organic layer was washed with a saturated aqueous solution of sodium chloride (50 mL), thereafter dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by a silica gel column to obtain tert-butyl (3E)-4-(3-amino-4-phenylphenyl)-3-butenoate (555.8 mg).

Aufarbeitung

  1. filtrationthe reaction mixture was filtered through celite
  2. washwashed with ethyl acetate (120 mL)
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-cb84ccb8ef9742119fd83111ef388a03
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09072734B2

Notizen zur Reaktion

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