Hydrochloric Acid → Dibenzofuran-4-boronic acid

HRID 1755508

Reaktionsgleichung

Reaktionsgleichung von HRID 1755508
CCCCCC.C([Li])CCC.CO[B:14]([O:17]C)[O:15]C.Cl.CCCCCC.Br[C:27]1[C:32]2[O:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[C:31]=2[CH:30]=[CH:29][CH:28]=1>O1CCCC1>[CH:30]1[C:31]2[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[O:33][C:32]=2[C:27]([B:14]([OH:15])[OH:17])=[CH:28][CH:29]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 8470Trimethyl borateHCID 4582564-Bromodibenzo[b,d]furanHCID 178418244HCID 178418244, Verbindung

Produkt 1

HCID 2734328Dibenzofuran-4-boronic acidAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a 300 ml three-necked flask, 7.2 g of 4-bromodibenzofuran was dissolved in −78° C. anhydrous tetrahydrofuran (THF) under an argon atmosphere. Then, 20 ml of an n-butyl lithium-n-hexane solution (1.6 M, 1.1 eq) was added and stirred for 1 hour. 4.23 ml (1.3 eq) of trimethoxyborane (B(OMe)3) was added and stirred for 2 hours, and the temperature of the reaction system was increased to room temperature. 200 ml of 1 N hydrochloric acid was added into the reactant and stirred for 3 hours. An organic layer was separated, and solvents were distilled off. In the crude product thus obtained, hexane was added. Precipitated product was filtered to obtain 4.94 g of dibenzofuran-4-boronic acid as a white solid (yield 80%). The product was measured by FAB-MS, and dibenzofuran-4-boronic acid having a molecular weight of 212 was detected.

Aufarbeitung

  1. stirringstirred for 2 hours
  2. stirringstirred for 3 hours
  3. customAn organic layer was separated
  4. distillationsolvents were distilled off
  5. customIn the crude product thus obtained
  6. filtrationPrecipitated product was filtered

Quellen und Nachweise

ORD-Eintrag
ord-eef586b16e714a5088e62021c813b531
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09172047B2

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