Carbon Dioxide → 5-Bromo-2,3-difluoro-4-(trimethylsilyl)benzoic acid

HRID 1879630

Reaktionsgleichung

Reaktionsgleichung von HRID 1879630
[Li]CCCC.CC1(C)CCCC(C)(C)N1.[Br:16][C:17]1[C:22]([Si:23]([CH3:26])([CH3:25])[CH3:24])=[C:21]([F:27])[C:20]([F:28])=[CH:19][CH:18]=1.[C:29](=[O:31])=[O:30]>C1COCC1.O>[Br:16][C:17]1[C:22]([Si:23]([CH3:24])([CH3:25])[CH3:26])=[C:21]([F:27])[C:20]([F:28])=[C:19]([CH:18]=1)[C:29]([OH:31])=[O:30]

Komponenten

7

Edukt 4

HCID 280Carbon DioxideHCID 130352,2,6,6-TetramethylpiperidineHCID 23070109(6-Bromo-2,3-difluorophenyl)trimethylsilaneHCID 178418339Butyllithium

Produkt 1

HCID 585380595-Bromo-2,3-difluoro-4-(trimethylsilyl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of n-BuLi (2.0 M in hexanes, 11.1 mL, 22.2 mmol) in anhydrous THF (17 mL) at −78° C. was added drop wise 2,2,6,6-tetramethylpiperidine (3.26 g, 22.1 mmol). After being stirred for 15 minutes, a solution of the product from step A (5.86 g, 22.1 mmol) in THF (20 mL) was added. The reaction mixture was stirred at −78° C. for 2 hours, then dry ice (100 g) was added. The mixture was allowed to stand at room temperature overnight, then it was diluted with water and extracted with EtOAc. The combined organics were dried over MgSO4, filtered, then concentrated to afford the title compound. The material was used directly in the next step without further purification. 1H NMR (500 MHz, CDCl3): δ 7.70 (d, J=4.4 Hz, 1H); 0.44 (s, 9H).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at −78° C. for 2 hours
  2. waitto stand at room temperature overnight
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a6c8e712035e4145a4b7fd1cc77e887a
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318667B2

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