反应 #80463

反应方程式

4-fluorobenzyl bromide

2-thiophenemethanol

NaOH

→

2-(4-fluorophenylmethoxymethyl)thiophene

收率 86.0%

溶剂

DMSO

brine

反应条件

后处理

1. 1
   萃取extracted with ether
2. 2
   洗涤The organic phase was washed with 1N aqueous H3PO4 (3×), H2O (3×), saturated aqueous NaHCO3 (2×), and brine
3. 3
   干燥dried over MgSO4
4. 4
   过滤filtered
5. 5
   浓缩concentrated in vacuo

实验过程

To a solution in DMSO (30 mL) of 4-fluorobenzyl bromide (3.27 mL, 26.3 mmol), 2-thiophenemethanol (3.00 mL, 31.7 mmol), and benzyltrimethylammonium chloride (244 mg, 1.31 mmol) was added NaOH (6.31 g, 159 mmol) and the reaction mixture was stirred for 17 hours at ambient temperature. The reaction mixture was poured into brine and extracted with ether. The organic phase was washed with 1N aqueous H3PO4 (3×), H2O (3×), saturated aqueous NaHCO3 (2×), and brine, dried over MgSO4, filtered, and concentrated in vacuo. Chromatography on silica gel (20% ethyl acetate/hexane) gave 2-(4-fluorophenylmethoxymethyl)thiophene (5.03 g, 86% ).

来源