2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → (2,3-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)trimethylsilane

HRID 407207

Reaktionsgleichung

Reaktionsgleichung von HRID 407207
C([Li])(CC)C.[F:6][C:7]1[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Si:14]([CH3:17])([CH3:16])[CH3:15].C(O[B:22]1[O:26][C:25]([CH3:28])([CH3:27])[C:24]([CH3:30])([CH3:29])[O:23]1)(C)C>C1COCC1>[F:6][C:7]1[C:12]([F:13])=[C:11]([B:22]2[O:26][C:25]([CH3:28])([CH3:27])[C:24]([CH3:30])([CH3:29])[O:23]2)[CH:10]=[CH:9][C:8]=1[Si:14]([CH3:17])([CH3:16])[CH3:15]

Komponenten

5

Edukt 3

HCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 108993711,2-Difluoro-3-trimethylsilylbenzeneHCID 178418400CID 53628100

Produkt 1

HCID 71150347(2,3-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)trimethylsilaneAusbeute 60,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-75 °C

Versuchsvorschrift

A solution of sec-butyllithium (1.4 M in cyclohexane; 19.17 mL, 26.8 mmol) was added to THF (53.7 mL) cooled to −75° C. To this solution was added (2,3-difluorophenyl)-trimethylsilane (prepared as in Heiss, C. et al. Eur. J. Org. Chem. 2007, 4, 669-675; 5.0 g, 26.8 mmol) dropwise keeping the temperature below −70° C. The resulting reaction mixture was stirred at −75° C. for 45 min after which time 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (5.49 g, 29.5 mmol) was added dropwise keeping the temperature below −70° C. The reaction mixture was then allowed to warm to 25° C. and was partitioned between Et2O and H2O. The aqueous phase was acidified to pH 3 with 12 Normal (N) HCl. The product was extracted with Et2O, and the organic phase was dried and concentrated under vacuum to provide the title compound as a white solid (5.03 g, 60%): 1H NMR (300 MHz, CDCl3) δ 7.42 (ddd, J=7.3, 4.4, 0.7 Hz, 1H), 7.09 (ddd, J=7.3, 4.1, 0.9 Hz, 1H), 1.36 (s, 12H), 0.32 (d, J=0.9 Hz, 9H); EIMS m/z 312.

Aufarbeitung

  1. customthe temperature below −70° C
  2. customThe resulting reaction mixture
  3. additionwas added dropwise
  4. customthe temperature below −70° C
  5. temperatureto warm to 25° C.
  6. customwas partitioned between Et2O and H2O
  7. extractionThe product was extracted with Et2O
  8. customthe organic phase was dried
  9. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-9d8cfe996d064397901a9eb59d1a9224
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754229B2

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