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Dimethylformamide → tert-Butyl (3-bromo-5-formylbenzyl)cyclopropylcarbamate

HRID 337634
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 337634
C([Li])CCC.C([Mg]Br)CCC.[CH:12]1([N:15]([CH2:23][C:24]2[CH:29]=[CH:28][C:27](Br)=[C:26]([Br:31])[CH:25]=2)[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:14][CH2:13]1.CN([CH:35]=[O:36])C>C1(C)C=CC=CC=1>[Br:31][C:26]1[CH:25]=[C:24]([CH:29]=[C:28]([CH:35]=[O:36])[CH:27]=1)[CH2:23][N:15]([CH:12]1[CH2:14][CH2:13]1)[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 66897118Tert-butyl cyclopropyl(3,4-dibromobenzyl)carbamateHCID 178418339ButyllithiumHCID 178418682HCID 178418682, Verbindung

Produkt 1

HCID 86651677tert-Butyl (3-bromo-5-formylbenzyl)cyclopropylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140
Toluene
Lösungsmittel

Versuchsvorschrift

To a toluene (0.1 M) solution of n-butyl lithium (2.5 M in hexanes, 1.2 eq.) was added at −10° C. n-butyl magnesium bromide (2.0 M in THF, 0.4 eq.). The resulting suspension was stirred at −10° C. for 20 min before tert-butyl cyclopropyl(3,4-dibromobenzyl)carbamate (1 eq., Amine 77, Step 2) was added. The now yellow-red suspension was stirred at 0° C. for 30 min before DMF (30 eq.) was added dropwise neat at −78° C. The reaction mixture was allowed to warm slowly to RT over 3 h. The now black suspension was quenched with 10% aq. HCl and then extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product by way of flash chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc) afforded the title compound as a golden yellow oil.

Aufarbeitung

  1. additionwas added
  2. additionwas added dropwise neat at −78° C
  3. customThe now black suspension was quenched with 10% aq. HCl
  4. extractionextracted with ether
  5. washThe combined organic extracts were washed further with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo
  9. customPurification of the crude product by way of flash chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-039442865f4c4b55aa51487a9e08b302
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08889714B2

Notizen zur Reaktion

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