Reaktion #2507860

Reaktionsgleichung

methyl 5-hydroxymethyl-thiophene-2-carboxylate

Bromine

imidazole

triphenylphosphine

→

title compound ( B )

Ausbeute 95.0%

Methyl 5-bromomethyl-thiophene-2-carboxylate

Ausbeute 95.0%

Lösungsmittel

CH2Cl2

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenthe reaction mixture was concentrated in vacuo
2. 2
   SonstigePurification of the crude residue by flash column chromatography on 80 g of silica gel (hexane →EtOAc, gradient)

Vorschrift

Bromine (0.47 mL, 9.12 mmol) was added to a solution of imidazole (617 mg, 9.06 mmol) and triphenylphosphine (2.40 g, 9.15 mmol) in CH2Cl2 (30 mL) at room temperature. A solution of methyl 5-hydroxymethyl-thiophene-2-carboxylate (prepared according to the procedures described in WO2004/037808; 1.30 g, 7.59 mmol) in CH2Cl2 (10 mL) was then added. After 10 min at room temperature, the reaction mixture was concentrated in vacuo. Purification of the crude residue by flash column chromatography on 80 g of silica gel (hexane →EtOAc, gradient) afforded 1.70 g (95%) of the title compound (B).

Quelle