反应 #2507860

反应方程式

methyl 5-hydroxymethyl-thiophene-2-carboxylate

Bromine

imidazole

triphenylphosphine

→

title compound ( B )

收率 95.0%

Methyl 5-bromomethyl-thiophene-2-carboxylate

收率 95.0%

溶剂

CH2Cl2

CH2Cl2

反应条件

后处理

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

实验过程

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).

来源