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Hydrochloric Acid → 4-(10-Phenylanthracen-9-yl)benzeneboronic acid

HRID 1910368
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1910368
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:14]([C:15]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[C:16]4[C:21]=2[CH:20]=[CH:19][CH:18]=[CH:17]4)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:4][CH:3]=1.C([Li])CCC.[B:33]([O:38]C)(OC)[O:34]C.Cl>O1CCCC1>[C:5]1([C:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:15]([C:22]3[CH:23]=[CH:24][C:25]([B:33]([OH:38])[OH:34])=[CH:26][CH:27]=3)=[C:16]3[C:21]=2[CH:20]=[CH:19][CH:18]=[CH:17]3)[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1
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Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 221382759-(4-Bromophenyl)-10-phenylanthraceneHCID 178418339Butyllithium

Produkt 1

HCID 235741214-(10-Phenylanthracen-9-yl)benzeneboronic acidAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

In a 500 mL three-neck flask were stirred 20 g (49 mmol) of 9-(4-Bromophenyl)-10-phenylanthracene obtained by the above Steps 1(1) to 1(4) and 300 mL of tetrahydrofuran (abbreviation: THF) in a nitrogen atmosphere at −78° C. Then, 34 mL (54 mmol) of n-butyllithium (1.6 mol/L hexane solution) was dropped, and this mixture was stirred for 2 hours at the same temperature. After that, 13 mL (110 mmol) of trimethyl borate was added therein, and the mixture was stirred for 24 hours at room temperature. After the reaction, 200 mL of 1.0 mol/L hydrochloric acid was added therein, and the mixture was stirred for 1 hour at room temperature. After that, an organic layer thereof was washed with water and separated into an organic layer and a water layer, and the obtained water layer was further extracted with ethyl acetate. This extracted solution and the organic layer were mixed and washed with saturated aqueous solution, and magnesium sulfate was added therein, so that moisture was removed. Then, suction filtration was performed so that a filtrate was obtained. The obtained filtrate was concentrated to provide a residue. The obtained residue was recrystallized with a mixed solution of chloroform and hexane, whereby 15 g of a powdery white solid of 4-(10-phenyl-9-anthryl)phenylboronic acid, which was the object of the synthesis, was obtained in a yield of 84% (synthesis scheme (a-5)).

Aufarbeitung

  1. stirringthe mixture was stirred for 24 hours at room temperature
  2. additionwas added
  3. stirringthe mixture was stirred for 1 hour at room temperature
  4. washAfter that, an organic layer thereof was washed with water
  5. customseparated into an organic layer
  6. extractiona water layer, and the obtained water layer was further extracted with ethyl acetate
  7. additionThis extracted solution and the organic layer were mixed
  8. washwashed with saturated aqueous solution, and magnesium sulfate
  9. additionwas added
  10. customso that moisture was removed
  11. filtrationThen, suction filtration
  12. customwas obtained
  13. concentrationThe obtained filtrate was concentrated
  14. customto provide a residue
  15. customThe obtained residue was recrystallized with a mixed solution of chloroform and hexane, whereby 15 g of a powdery white solid of 4-(10-phenyl-9-anthryl)phenylboronic acid, which
  16. customthe object of the synthesis
  17. customwas obtained in a yield of 84% (synthesis scheme (a-5))

Quellen und Nachweise

ORD-Eintrag
ord-1262bb8e26074f819a3410853f9c3a09
Quelldatensatz
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08603644B2

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