Reaktion #512240

Reaktionsgleichung

4-(5-bromo-2-chlorobenzoyl)phenethyl acetate

borontrifluoride diethylether

triethylsilane

→

4-(5-bromo-2-chlorobenzyl)phenethyl acetate

Ausbeute 65.0%

Lösungsmittel

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction vessel was cooled to room temperature
2. 2
   ExtraktionThe product was extracted with ethyl acetate (2×25 mL)
3. 3
   Waschenwashed with brine (25 mL)
4. 4
   Trocknendried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated
7. 7
   SonstigePurification on silica gel using an ISCO column with 5% ethyl acetate in hexane
8. 8
   Sonstigegave intermediate BG (620 mg, yield 65%)

Vorschrift

A mixture of 4-(5-bromo-2-chlorobenzoyl)phenethyl acetate (intermediate BF) (1 g, 2.62 mmol), borontrifluoride diethylether (0.65 mL, 10.4 mmol) and triethylsilane (0.84 mL, 10.4 mmol) was heated at 85° C. for 2 h in a sealed tube. The reaction vessel was cooled to room temperature and ice-water (50 mL) was added. The product was extracted with ethyl acetate (2×25 mL), washed with brine (25 mL), dried (Na2SO4), filtered and evaporated. Purification on silica gel using an ISCO column with 5% ethyl acetate in hexane gave intermediate BG (620 mg, yield 65%). 1H NMR (300 MHz, CDCl3): δ 7.27-7.10 (m, 7H), 4.27 (t, J=6.9, 7.2 Hz, 2H), 4.03 (s, 2H), 2.92 (t, J=6.9, 7.2 Hz, 2H), 2.05 (s, 3H).

Quelle