Reaktion #2445046

Reaktionsgleichung

7-bromo-3-phenyl-1H-indene

3-phenyl-1H-inden-7-ol

K3PO4

N-{2′-[di(tert-butyl)phosphino][1,1′-biphenyl]-2-yl}-N,N-dimethylamine

→

bis(3-phenyl-1H-inden-7-yl)ether

Lösungsmittel

water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Sonstigethe organic layer was separated
3. 3
   Extraktionthe aqueous layer was extracted with 3×75 ml of CH2Cl2
4. 4
   ExtraktionThe combined extract
5. 5
   Waschenwas washed with 2×100 ml of water
6. 6
   Trocknendried over K2CO3
7. 7
   Sonstigeevaporated to dryness

Vorschrift

Under an argon atmosphere, to a mixture of 6.90 g (25.5 mmol) of 7-bromo-3-phenyl-1H-indene, 5.30 g (25.5 mmol) of 3-phenyl-1H-inden-7-ol, 10.8 g (51 mmol) K3PO4, and 100 ml of toluene, a mixture of 300 mg (0.52 mmol) Pd(dba)2 and 348 mg (1.02 mmol) of N-{2′-[di(tert-butyl)phosphino][1,1′-biphenyl]-2-yl}-N,N-dimethylamine was added. This mixture was stirred for 8 hours at 100° C. Then, 300 ml of water was added, the organic layer was separated, and the aqueous layer was extracted with 3×75 ml of CH2Cl2. The combined extract was washed with 2×100 ml of water, dried over K2CO3, and evaporated to dryness. The analytically pure product, bis(3-phenyl-1H-inden-7-yl)ether, was obtained using flash chromatography on Silica Gel 60 (40-63 μm, d 50 mm, 1250 mm, eluant: CH2Cl2). Yield, 3.56 g (35%) of a white solid.

Quelle