反応 #80442

反応方程式

ammonium chloride

furan

4-fluorobenzyl bromide

n-butyllithium

hexane

→

2-(4-fluorophenylmethyl)furan

収率 81.2%

溶媒

THF

ether

THF

反応条件

後処理

1. 1
   その他transferred by cannula to a stirred -78° C.
2. 2
   workup.WAITThe transfer was made under nitrogen over a period of 30-40 minutes
3. 3
   workup.STIRRINGThe reaction mixture was stirred at ambient temperature overnight
4. 4
   抽出the mixture extracted with ether
5. 5
   乾燥The ether layer was dried (MgSO4)
6. 6
   濃縮concentrated in vacuo
7. 7
   workup.DISTILLATIONthe residue distilled at reduced pressure

実験手順

To a 0° C. solution of furan (13.6 g, 0.20 mol) in a mixture of anhydrous ether (230 mL) and anhydrous THF (70 mL) under nitrogen was added a 2.5M solution of n-butyllithium in hexane (54.0 mL, 0.134 mol). The mixture was stirred at 0° C. for 1.5 hours and then transferred by cannula to a stirred -78° C. solution of 4-fluorobenzyl bromide (23.6 g, 0.125 mol) and tetrakis-(triphenylphosphine)palladium (O) (1.25 g, 0.001 mol) in anhydrous THF (200 mL). The transfer was made under nitrogen over a period of 30-40 minutes. The reaction mixture was stirred at ambient temperature overnight, saturated aqueous solution of ammonium chloride was added and the mixture extracted with ether. The ether layer was dried (MgSO4), concentrated in vacuo and the residue distilled at reduced pressure to give 2-(4-fluorophenylmethyl)furan as a colorless oil (17.89 g, 81% ). b.p. 57°-62° C. at 0.5-0.7 mm-Hg.

出典