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4-Chlorophenylboronic acid → 3-[2-(4'-Chloro-1,1'-biphenyl-4-yl)ethyl]-1,3-oxazolidine-2,4-dione

HRID 1867535
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1867535
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[C:14](=[O:15])[CH2:13][O:12][C:11]2=[O:16])=[CH:4][CH:3]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]3[C:14](=[O:15])[CH2:13][O:12][C:11]3=[O:16])=[CH:4][CH:3]=2)=[CH:20][CH:19]=1
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Komponenten

6

Edukt 3

HCID 742994-Chlorophenylboronic acidHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 675289483-[2-(4-Bromophenyl)ethyl]-1,3-oxazolidine-2,4-dione

Produkt 1

HCID 675285133-[2-(4'-Chloro-1,1'-biphenyl-4-yl)ethyl]-1,3-oxazolidine-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Katalysator
HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A 250 ml three-necked round-bottomed flask placed under an inert atmosphere is charged with 2 g (7.04 mmol) of 3-[2-(4-bromophenyl)ethyl]-1,3-oxazolidine-2,4-dione, obtained in step 3.1., 2.2 g (14.08 mmol) of 4-chlorophenylboronic acid and 6.5 g (28.16 mmol) of potassium phosphate hydrate in suspension in 100 ml of 1,2-dimethoxyethane. Subsequently 0.80 g (0.70 mmol) of palladium tetrakis(triphenylphosphine) is added. The reaction mixture is subsequently refluxed overnight. The salts are separated by filtration over Celite and then the filtrate is concentrated under reduced pressure. The residue is taken up in ethyl acetate and water. The organic phase is separated and is washed with saturated aqueous sodium chloride solution. The filtrate is concentrated under reduced pressure and the residue is purified by chromatography on silica gel, eluting with dichloromethane.

Aufarbeitung

  1. customA 250 ml three-necked round-bottomed flask placed under an inert atmosphere
  2. customobtained in step 3.1
  3. customThe salts are separated by filtration over Celite
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customThe organic phase is separated
  6. washis washed with saturated aqueous sodium chloride solution
  7. concentrationThe filtrate is concentrated under reduced pressure
  8. customthe residue is purified by chromatography on silica gel
  9. washeluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-b6033f8aeb1040af830aaf00e75e3a75
Quelldatensatz
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07632850B2

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