Reaction #554597

Reaction equation

3-bromoanisole

2-biphenylboronic acid

sodium carbonate

→

3-methoxy[1,1′:2′,1″]terphenyl

Yield 90.0%

Solvents

dimethyl ether

Conditions

Workup

1. 1
   Temperaturethe resultant was refluxed
2. 2
   Temperaturewhile heating for 8 hours
3. 3
   Otheran aqueous phase was removed
4. 4
   WashAn organic phase was washed with water and saturated brine
5. 5
   Dryingdried with magnesium sulfate
6. 6
   FiltrationAfter the magnesium sulfate was filtered out
7. 7
   Concentrationthe organic phase was concentrated
8. 8
   OtherThe resulting residue was purified by means of silica gel column chromatography

Procedure

Under an argon atmosphere, 18.7 g of 3-bromoanisole, 23.8 g of 2-biphenylboronic acid and 2.31 g of tetraxis(triphenylphosphine)palladium(0) were placed in a flask. 340 mL of dimethyl ether (DME) and 170 mL of a 2M aqueous sodium carbonate solution were added to this flask, and the resultant was refluxed with stirring while heating for 8 hours. After cooling to room temperature, an aqueous phase was removed. An organic phase was washed with water and saturated brine, and then dried with magnesium sulfate. After the magnesium sulfate was filtered out, the organic phase was concentrated. The resulting residue was purified by means of silica gel column chromatography, whereby 23.4 g (yield: 90%) of intended 3-methoxy[1,1′:2′,1″]terphenyl was obtained.

Source