Reaktion #833936

Reaktionsgleichung

NaHCO3

(tert-butoxy)-N-[2-(4-bromophenyl)(3-thiophenyl)]carboxamide

HCl

H2O

→

2-(4-bromo-phenyl)-thiophen-3-yl amine

Ausbeute 74.0%

Lösungsmittel

EtOAc

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionExtract the mixture with EtOAc (3×100 mL)
2. 2
   Sonstigedry
3. 3
   Einengenconcentrate
4. 4
   Sonstigeto give a slightly colored solid
5. 5
   SonstigePurification of the crude material by flash chromatography (Silica gel-Hexane/AcOEt 49:1

Vorschrift

Treat dropwise a solution of (tert-butoxy)-N-[2-(4-bromophenyl)(3-thiophenyl)]carboxamide (10.8 g, 0.3 mol) in EtOAc (75 mL) at 0° C. with 244 mL (8 mL/mmol) of freshly prepared 1N HCl in EtOAc and stir the mixture at room temperature overnight. Dissolve the white precipitate with H2O (100 mL) and neutralize with a NaHCO3 saturated solution. Extract the mixture with EtOAc (3×100 mL) and combine organic, dry and concentrate to give a slightly colored solid. Purification of the crude material by flash chromatography (Silica gel-Hexane/AcOEt 49:1 then 9:1) furnishes 5.7 g (74%) of 2-(4-bromo-phenyl)-thiophen-3-yl amine as a pale yellow solid.

Quelle