Reaktion #1352465

Reaktionsgleichung

2,6-dibromoaniline

Na2CO3

4-trifluoromethylphenyl boronic acid

→

4,4″-Bis-trifluoromethyl-[1,1′;3′,1″]terphenyl-2′-ylamine

Ausbeute 93.5%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas immersed in a 110° C.
2. 2
   Extraktionextracted with ether
3. 3
   WaschenThe organic layer was washed with brine
4. 4
   Trocknendried over Na2SO4
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe residue was purified by flash chromatography (SiO2, 2.5-5.0% EtOAc/Heptane)

Vorschrift

A suspension of tetrakis(triphenylphosphine) palladium(0) (66 mg, 0.06 mmol) in toluene (8 mL) was treated with 2,6-dibromoaniline (500 mg, 2.0 mmol), aqueous Na2CO3 (2M, 3.98 mL), and 4-trifluoromethylphenyl boronic acid (831 mg, 4.4 mmol). The resulting suspension was immersed in a 110° C. oil bath, and stirred under Ar for 22 h. The suspension was cooled to rt, and extracted with ether. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, 2.5-5.0% EtOAc/Heptane) to afford 4,4″-Bis-trifluoromethyl-[1,1′;3′,1″]terphenyl-2′-ylamine (713 mg, 93%): 1H NMR (CDCl3, chemical shifts in ppm relative to TMS): 6.93 (t, 1H, J=7.3 Hz), 7.14 (d, 2H, J=7.3 Hz), 7.64 (d, 4H, J=8.0 Hz), 7.74 (d, 4H, J=8.0 Hz).

Quelle