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Acetic Acid → (5-Bromo-2-fluorophenyl)boronic acid

HRID 974420
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 974420
Br[C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[F:9].[Mg].C[O:12][B:13](OC)[O:14]C.C(O)(=O)C>O1CCCC1.C(OCC)C.O>[OH:12][B:13]([OH:14])[C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[F:9]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 8470Trimethyl borateHCID 150342,4-Dibromo-1-fluorobenzeneHCID 5462224Magnesium2×

Produkt 1

HCID 10856974(5-Bromo-2-fluorophenyl)boronic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel
HCID 3283
Diethyl Ether
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of 2,4-dibromofluorobenzene (12.7 g, containing 30% 3,4-dibromofluorobenzene) in dry tetrahydrofuran (THF) (10 ml) is added over 5 min to a stirred suspension of magnesium turnings (1.15 g) in dry THF (50 ml) under an atmosphere of nitrogen and cooled in a water bath. After 1 hour, when all the magnesium has reacted, this reagent is added over 20 min to a stirred solution of trimethoxyborane (7 ml) in dry diethyl ether (80 ml) under an atmosphere of nitrogen and cooled at -78° C. The mixture is stirred at -78° C. for a further 15 min. and glacial acetic acid (6 ml) added followed by water (50 ml). The mixture is warmed to room temperature, extracted with diethyl ether (x3), washed with water, dried and the solvent evaporated under reduced pressure. The residue is stirred with carbon tetrachloride (30 ml) and then cooled at 0° C. The crystals of dihydroxy-(5-bromo-2-fluorophenyl)-borane are filtered off and washed with a little carbon tetrachloride. Yield 2.8 g m.pt. 173°-174° C.

Aufarbeitung

  1. temperaturecooled in a water bath
  2. temperatureThe mixture is warmed to room temperature
  3. extractionextracted with diethyl ether (x3)
  4. washwashed with water
  5. customdried
  6. customthe solvent evaporated under reduced pressure
  7. stirringThe residue is stirred with carbon tetrachloride (30 ml)
  8. temperaturecooled at 0° C
  9. filtrationThe crystals of dihydroxy-(5-bromo-2-fluorophenyl)-borane are filtered off
  10. washwashed with a little carbon tetrachloride

Quellen und Nachweise

ORD-Eintrag
ord-d0b36f5592834850b6e069f49a1c7930
Quelldatensatz
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05068403

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