Reaktion #79853

Reaktionsgleichung

triethylamine

4-bromo-2-chlorophenol

phenyl boronic acid

Hypersil

→

4-Bromo-2-chloro-1-phenoxybenzene

Lösungsmittel

heptane

dichloromethane

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered through a bed of celite
2. 2
   EinengenThe filtrate was concentrated under reduced pressure
3. 3
   Sonstigeto remove dichloromethane
4. 4
   ExtraktionThe mixture was extracted with IN hydrochloric acid, 15 wt % aqueous sodium hydroxide, brine
5. 5
   Trocknendried over magnesium sulfate
6. 6
   FiltrationThe mixture was filtered
7. 7
   Einengenthe filtrate concentrated under reduced pressure
8. 8
   Sonstigeto provide (1.27 g, 45%)
9. 9
   Sonstigetr 14.42min.

Vorschrift

A mixture of 4-bromo-2-chlorophenol (2.07 g, 10 mmol), phenyl boronic acid (3.66 g, 30 mmol), copper(II) acetate (2.0 g, 1.1 mmol) and 4A powdered molecular sieves (20 g) in dichloromethane (100 mL) was treated with triethylamine (5.0 g, 50 mmol) then stirred at ambient temperature for 5 days. The mixture was diluted with heptane (100 mL), then filtered through a bed of celite. The filtrate was concentrated under reduced pressure to remove dichloromethane. The mixture was extracted with IN hydrochloric acid, 15 wt % aqueous sodium hydroxide, brine and then dried over magnesium sulfate. The mixture was filtered and the filtrate concentrated under reduced pressure to provide (1.27 g, 45%): 1H NMR (DMSO-d6, 400 MHz) δ 7.87(s, 1H), 7.55(d, 1H), 7.40(t, 2H), 7.17(t, 1H), 6.99(m, 3H); MS MH+283; RP-HPLC (Hypersil HS, 5 μm, 100 A 4.6×250 mm; 25%-100% acetonitrile—0.05 M ammonium acetate over 10 min, 1 m/min) tr 14.42min.

Quelle