Cesium carbonate → tert-Butyl 2-(4-bromo-3,5-dimethylphenoxy)ethylcarbamate

HRID 237528Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 237528
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].Br[CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:4][C:3]=1[CH3:10]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonate3×HCID 819704-Bromo-3,5-dimethylphenolHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate3×

Produkt 1

HCID 86697191tert-Butyl 2-(4-bromo-3,5-dimethylphenoxy)ethylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-bromo-3,5-dimethylphenol (200 mg) in N,N-dimethylformamide (5 mL) is added tert-butyl 2-bromoethylcarbamate (270 mg) and Cs2CO3 (810 mg). The mixture is stirred for 20 hours at room temperature. tert-Butyl 2-bromoethylcarbamate (110 mg) and Cs2CO3 (325 mg) are added and the mixture is stirred for 4 hours. Again tert-butyl 2-bromoethylcarbamate (110 mg) and Cs2CO3 (325 mg) are added and the mixture is stirred for 12 hours. The mixture is partitioned between water and diethylether. The organic phase is washed with brine and dried (MgSO4). The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→80:20) to give the title compound. Yield: 320 mg; LC (method 8): tR=0.66 min; Mass spectrum (ESI+): m/z=344 [M+H]+.

Aufarbeitung

  1. stirringthe mixture is stirred for 4 hours
  2. stirringthe mixture is stirred for 12 hours
  3. customThe mixture is partitioned between water and diethylether
  4. washThe organic phase is washed with brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent is evaporated
  7. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→80:20)

Quellen und Nachweise

ORD-Eintrag
ord-c710cc577eaf45ca9a879dbc21c435e7
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642585B2

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