反応 #2460322

反応方程式

water

DMF

4-bromophenyl n-butyl sulfide

nBuLi

THF

→

4-butylthiobenzaldhyde

反応条件

後処理

1. 1
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 2 hours
2. 2
   抽出the product was extracted three times by ether (3×50 ml)
3. 3
   乾燥the combined organic layer was dried over magnesium sulfate
4. 4
   その他After removal of solvent under reduced pressure
5. 5
   その他the product was purified by flash chromatography column
6. 6
   その他isolated in 66.7% (0.88 g)
7. 7
   その他yield

実験手順

To a solution of 4-bromophenyl n-butyl sulfide (1.5 g, 6.12 mmol) in 60 ml of dry THF was added nBuLi (4.1 ml, 1.6 M in hexanes) at −78° C. under nitrogen. The mixture was stirred for 1 hour at −78° C. and then DMF (2.0 ml) was added. The reaction mixture was stirred at room temperature for 2 hours. Then 40 ml of water was added to this mixture, the product was extracted three times by ether (3×50 ml) and the combined organic layer was dried over magnesium sulfate. After removal of solvent under reduced pressure, the product was purified by flash chromatography column using 10% of ethyl acetate in hexanes as eluant and isolated in 66.7% (0.88 g) yield.1H NMR (CDCl3, 500 MHz) δppm: 9.98 (s, 1H, CHO), 7.77 (d, J=8.5 Hz, 2H), 7.36 (d, J=8.5 Hz, 2H,), 7.11 (s, 2H), 3.02 (t, J=7.2 Hz, 2H, CH2), 1.71 (m, 2H, CH2), 1.50 (m, 2H, CH2), 0.97 (t, J=7.5 Hz, 6H, CH3).

出典