5,6-Dibromo-1,3-dioxaindane → 5-(4-Fluorophenyl)-6-[4-(methylthio)phenyl]-1,3-benzodioxole

HRID 1839935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1839935
Br[C:2]1[C:10](Br)=[CH:9][C:5]2[O:6][CH2:7][O:8][C:4]=2[CH:3]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.[CH3:22][S:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[C:10]([C:27]3[CH:28]=[CH:29][C:24]([S:23][CH3:22])=[CH:25][CH:26]=3)=[CH:9][C:5]3[O:6][CH2:7][O:8][C:4]=3[CH:3]=2)=[CH:15][CH:14]=1

Komponenten

7

Edukt 3

HCID 2258145,6-Dibromo-1,3-dioxaindaneHCID 2856454-Fluorophenylboronic acidHCID 27339594-(Methylthio)phenylboronic acid

Produkt 1

HCID 108308475-(4-Fluorophenyl)-6-[4-(methylthio)phenyl]-1,3-benzodioxoleAusbeute 142,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Under nitrogen, 1 g of Pd(PPh3)4 was added to a stirred solution of 4 g (14.3 mmol) of 5,6-dibromo-1,3-benzodioxole (Lancaster), 2.4 g (17.2 mmol) of 4-fluorophenylboronic acid, and 2.87 g (17.2 mmol) of 4-methylthiophenylboronic acid (Example 1, Step 2) in 70 mL of toluene, 40 mL of ethanol, and 30 mL of 2M Na2C03. After vigorous stirring at reflux overnight, the solvent was removed in vacuo. The residue was dissolved in ethyl acetate, washed with water, and dried over Na2SO4. Concentration in vacuo gave 6.9 g of 5-(4-fluorophenyl)-6-[4-(methylthio)phenyl]-1,3-benzodioxole as a semi-solid which was used without further purification.

Aufarbeitung

  1. temperatureat reflux overnight
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. concentrationConcentration in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-976feb575ade4316bd21322dbcfac058
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06677488B2

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