반응 #79853

반응 방정식

triethylamine

4-bromo-2-chlorophenol

phenyl boronic acid

Hypersil

→

4-Bromo-2-chloro-1-phenoxybenzene

용매

heptane

dichloromethane

acetonitrile

반응 조건

후처리

1. 1
   여과filtered through a bed of celite
2. 2
   농축The filtrate was concentrated under reduced pressure
3. 3
   기타to remove dichloromethane
4. 4
   추출The mixture was extracted with IN hydrochloric acid, 15 wt % aqueous sodium hydroxide, brine
5. 5
   건조dried over magnesium sulfate
6. 6
   여과The mixture was filtered
7. 7
   농축the filtrate concentrated under reduced pressure
8. 8
   기타to provide (1.27 g, 45%)
9. 9
   기타tr 14.42min.

실험 절차

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.

출처