Pinacol → 2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

HRID 1396534Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1396534
[F:1][C:2]1[CH:3]=[C:4]([B:10]([OH:12])[OH:11])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].O[C:14]([C:17](O)([CH3:19])[CH3:18])([CH3:16])[CH3:15]>C1CCCCC1>[F:1][C:2]1[CH:3]=[C:4]([B:10]2[O:12][C:17]([CH3:19])([CH3:18])[C:14]([CH3:16])([CH3:15])[O:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Komponenten

4

Edukt 2

HCID 6425PinacolHCID 2783130(4-Cyano-3-fluorophenyl)boronic acid

Produkt 1

HCID 513509512-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrileAusbeute 85,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8078CyclohexaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A suspension of the crude 3-fluoro-4-cyanophenyl boronic acid (9.2 Kg, 55.8 mol) in cyclohexane (150 L) was treated with pinacol (13.2 Kg, 111.6 mol, 2.0 equiv) at room temperature, and the resulting reaction mixture was warmed to 40° C. for 4 h. When TLC and LC/MS showed that the reaction was deemed complete, the reaction mixture was cooled down to room temperature before being washed with water (2×75 L). The organic layer was then dried over magnesium sulfate (MgSO4) and concentrated under the reduced pressure to afford 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (19, 11.8 Kg, 13.8 Kg theoretical, 85.6% yield) as a light yellow solid. For 19: 1H NMR (300 MHz, DMSO-d6) δ ppm 7.92 (t, 1H, J=7.00 Hz), 7.62 (m, 2H), 1.29 (s, 12H).

Aufarbeitung

  1. customthe resulting reaction mixture
  2. temperaturethe reaction mixture was cooled down to room temperature
  3. washbefore being washed with water (2×75 L)
  4. dry with materialThe organic layer was then dried over magnesium sulfate (MgSO4)
  5. concentrationconcentrated under the reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5006a6a9c26b4d71ae57c5ea0b9f1068
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901123B2

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