反応 #58844

反応方程式

water

3-iodo-bromobenzene

4-butyne-1-ol

triethylamine

→

4-(3-bromophenyl)but-3-yn-1-ol

収率 92.0%

溶媒

DMF

反応条件

後処理

1. 1
   抽出extracted with EtOAc
2. 2
   洗浄The combined extracts were washed sequentially with water and brine
3. 3
   乾燥dried over Na2SO4
4. 4
   濃縮concentrated at reduced pressure
5. 5
   濃縮Chromatography of the resultant concentrate on silica gel with a gradient of 5% to 30% EtOAc-hexanes

実験手順

A solution of 10.0 gm (35.3 mmol) of 3-iodo-bromobenzene in DMF was treated with 2.95 mL (88 mmol) of 4-butyne-1-ol, 0.2 gm (1.06 mmol) of copper (I) iodide, 1.23 gm of dichlorobis(triphenylphosphine)-palladium(II), and 49 mL (0.35 mol) of triethylamine, stirred at room temperature for 18 h, poured into water and extracted with EtOAc. The combined extracts were washed sequentially with water and brine, dried over Na2SO4 and concentrated at reduced pressure. Chromatography of the resultant concentrate on silica gel with a gradient of 5% to 30% EtOAc-hexanes afforded 4-(3-bromophenyl)but-3-yn-1-ol as an orange oil, 7.3 gm (92% yield); 1H NMR (400 MHz, CDCl3) δ: 1.79 (s, 1H), 2.67 (t, 2H, J=6.3 Hz), 3.80 (t, 2H, J=6.3 Hz), 7.14 (t, 1H, J=7.9 Hz), 7.30 (d, 1H, J=7.9 Hz), 7.41 (m, 1H), 7.54 (t, 1H, J=1.6 Hz).

出典