Benzoyl chloride, 3-nitro- → Tert-butyl 3-nitrobenzoate

HRID 1599098

Reaktionsgleichung

Reaktionsgleichung von HRID 1599098
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[K+].[N+:7]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13](Cl)=[O:14])([O-:9])=[O:8]>O1CCCC1>[C:2]([O:4][C:13](=[O:14])[C:12]1[CH:16]=[CH:17][CH:18]=[C:10]([N+:7]([O-:9])=[O:8])[CH:11]=1)([CH3:5])([CH3:3])[CH3:1]

Komponenten

4

Edukt 2

HCID 8495Benzoyl chloride, 3-nitro-HCID 23665647Potassium tert-butoxide

Produkt 1

HCID 11961369Tert-butyl 3-nitrobenzoateAusbeute 63,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Potassium t-butoxide solid (3.82 g, 32.30 mmol) was added to a solution of 3-nitrobenzoyl chloride (5.00 g, 26.94 mmol) in dry tetrahydrofuran (70 mL) and stirred under nitrogen for 2 hrs. The reaction mixture was concentrated in vacuo and partitioned between dichloromethane and water. After separating the phases, the aqueous layer was back-extracted with ethyl acetate. The organic layers were combined, dried over anhydrous magnesium sulfate, filtered and then concentrated in vacuo. The crude product was purified on flash grade silica gel using 0-5% gradient of ethyl acetate in n-hexane. Fractions containing the product were combined, concentrated in vacuo, and then dried under high vacuum to provide 3.82 g of the title compound as an oil. 1H NMR (300 MHz, CDCl3) d 8.79 (m, 1H), 8.35 (m, 2H), 7.62 (m, 1H), 1.63 (s, 9H); low resolution MS (Cl) m/e 224 (MH+).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompartitioned between dichloromethane and water
  3. customAfter separating the phases
  4. extractionthe aqueous layer was back-extracted with ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified on flash grade silica gel using 0-5% gradient of ethyl acetate in n-hexane
  9. additionFractions containing the product
  10. concentrationconcentrated in vacuo
  11. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3ba72393137a4e0d8e5cddb209939684
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05739129

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