反応 #80463

反応方程式

4-fluorobenzyl bromide

2-thiophenemethanol

NaOH

→

2-(4-fluorophenylmethoxymethyl)thiophene

収率 86.0%

溶媒

DMSO

brine

反応条件

後処理

1. 1
   抽出extracted with ether
2. 2
   洗浄The organic phase was washed with 1N aqueous H3PO4 (3×), H2O (3×), saturated aqueous NaHCO3 (2×), and brine
3. 3
   乾燥dried over MgSO4
4. 4
   ろ過filtered
5. 5
   濃縮concentrated in vacuo

実験手順

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% ).

出典