1-Bromo-4-fluorobenzene → 1-BOC-4-(4-bromophenoxy)piperidine

HRID 912731

Reaktionsgleichung

Reaktionsgleichung von HRID 912731
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[Br:15][C:16]1[CH:21]=[CH:20][C:19](F)=[CH:18][CH:17]=1.[H-].[Na+]>CN(C)C=O>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 99931-Bromo-4-fluorobenzeneHCID 24758Sodium hydrideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Produkt 1

HCID 467390061-BOC-4-(4-bromophenoxy)piperidineAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of 2.01 g (10 mmol) of 1,1-dimethylethyl 4-hydroxy-1-piperidinecarboxylate in 20 ml of dimethylformamide is admixed with 7 g (40 mmol) of 1-bromo-4-fluorobenzene and 2.5 g (50 mmol) of sodium hydride at 50% in mineral oil. The mixture is stirred at 100° C. for 3 hours and then evaporated to dryness. The residue is taken up in 50 ml of ice-water and extracted with dichloromethane. The organic extracts are evaporated to dryness, to give 3.5 g of an oily product, which is used as it is in the following step.

Aufarbeitung

  1. customevaporated to dryness
  2. extractionextracted with dichloromethane
  3. customThe organic extracts are evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-0f140603e0394309894e324b9534237a
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026258B2

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