Hydrochloric Acid → [4-Methyl-3-(trifluoromethyl)phenyl]boronic acid

HRID 1642841Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1642841
C([Li])CCC.[CH3:6][C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][C:8]=1[C:14]([F:17])([F:16])[F:15].C[O:19][B:20](C)[O:21]C.Cl>CCCCCC.C1COCC1>[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([B:20]([OH:21])[OH:19])=[CH:9][C:8]=1[C:14]([F:17])([F:16])[F:15]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 138991Boronic acid, methyl-, dimethyl esterHCID 27756354-Methyl-3-(trifluoromethyl)bromobenzeneHCID 178418339Butyllithium

Produkt 1

HCID 45158669[4-Methyl-3-(trifluoromethyl)phenyl]boronic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

At −78° C., 9.2 ml (1.5 g, 23.0 mmol) of a 2.5M solution of n-butyllithium in hexane were initially charged in 30 ml of THF. 5.0 g (20.9 mmol) of 4-methyl-3-(trifluoromethyl)bromobenzene were dissolved in 15 ml of THF and slowly added dropwise. 3.3 g (31.4 mmol) of trimethylboronic acid were then added dropwise. The mixture was stirred at −78° C. for 2 h, and 11 ml of 2 N hydrochloric acid were then added. The mixture was allowed to warm to RT, and the organic phase was separated off. The solvent was removed under reduced pressure and the residue was recrystallized from n-heptane. Yield: 2.6 g (60% of theory)

Aufarbeitung

  1. additionslowly added dropwise
  2. temperatureto warm to RT
  3. customthe organic phase was separated off
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was recrystallized from n-heptane

Quellen und Nachweise

ORD-Eintrag
ord-e14c8e68c695457686e0ff4e8e86daf4
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119663B2

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