Cyclobutanone → 2-Bromo-5-(1-hydroxycyclobutyl)benzonitrile

HRID 338388Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338388
[Br:1][C:2]1[CH:9]=[CH:8][C:7](I)=[CH:6][C:3]=1[C:4]#[N:5].C([Mg]Cl)(C)C.[Cl-].[Li+].[C:18]1(=[O:22])[CH2:21][CH2:20][CH2:19]1>O1CCCC1.O>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([C:18]2([OH:22])[CH2:21][CH2:20][CH2:19]2)=[CH:6][C:3]=1[C:4]#[N:5]

Komponenten

7

Edukt 4

HCID 14496CyclobutanoneHCID 433294Lithium ChlorideHCID 450407122-Bromo-5-iodobenzonitrileHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 866987292-Bromo-5-(1-hydroxycyclobutyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

To 2-bromo-5-iodobenzonitrile (1457 mg, 4.730 mmol) in tetrahydrofuran (10 mL) at −40° C. was added isopropyl magnesium chloride.lithium chloride (1.3M in THF, 4.4 mL, 5.7 mmol) dropwise. The mixture was stirred at −40° C. for 10 minutes, and was then treated with cyclobutanone (0.4 mL, 5.2 mmol) dropwise at −40° C. The reaction mixture was warmed to room temperature and stirred at that temperature for 16 hours. The reaction mixture was poured into water (10 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to give the title compound which was used directly in the next step without further purification.

Aufarbeitung

  1. temperatureThe reaction mixture was warmed to room temperature
  2. stirringstirred at that temperature for 16 hours
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0775dc3269994b5da2b902618f009bc0
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889730B2

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