Reaktion #58845

Reaktionsgleichung

sodium bicarbonate

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

DAST

→

1-Bromo-3-(4-fluoro-but-1-ynyl)benzene

Ausbeute 64.0%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to room temperature for 1 h
2. 2
   Extraktionextracted with EtOAc
3. 3
   WaschenThe combined extracts were washed sequentially with water and brine
4. 4
   Trocknendried over Na2SO4
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   EinengenChromatography of the resultant concentrate on silica gel with a gradient of 0% to 24% EtOAc-hexanes

Vorschrift

A solution of 1.5 gm (6.67 mmol) of 4-(3-bromophenyl)but-3-yn-1-ol in CH2Cl2 at 0° C. was treated with 2.0 mL (15.3 mmol) of DAST, stirred at 0° C. for 1 h, allowed to warm to room temperature for 1 h, poured into saturated sodium bicarbonate and extracted with EtOAc. The combined extracts were washed sequentially with water and brine, dried over Na2SO4 and concentrated under reduced pressure. Chromatography of the resultant concentrate on silica gel with a gradient of 0% to 24% EtOAc-hexanes gave 1-Bromo-3-(4-fluoro-but-1-ynyl)benzene as a volatile liquid, 0.96 gm (64% yield); 1H NMR (400 MHz, CDCl3) δ: 2.82 (dt, 2H, J=6.6, 19.8 Hz), 4.56 (dt, 2H, J=6.6,46.4 Hz), 7.14 (t, 2H, J=7.9 Hz), 7.31 (m, 1H), 7.41 (m, 1H), 7.55 (t, 1H, J=1.7 Hz).

Quelle