반응 #10166

반응 방정식

water

potassium carbonate

methyl 2-iodobenzoate

4-cyano-phenylboronic acid

→

methyl 4′-cyano-1,1′-biphenyl-2-carboxylate

수율 86.0%

용매

THF

반응 조건

후처리

1. 1
   온도This mixture was heated
2. 2
   온도to reflux for 3.5 hours
3. 3
   기타The solvent was then removed under reduced pressure
4. 4
   추출The organic layer was extracted with additional EtOAc
5. 5
   세척The combined organics were washed with water
6. 6
   건조The organics were then dried over sodium sulfate
7. 7
   여과filtered
8. 8
   농축concentrated
9. 9
   기타to obtain the crude product
10. 10
    세척eluting with 8:1 heptane

실험 절차

To 500 mL of THF was added water (18.4 mL, 1.02 mol), potassium carbonate (70.5 g, 0.510 mol), methyl 2-iodobenzoate (53.5 g, 0.204 mol), 4-cyano-phenylboronic acid (30.0 g, 0.204 mol) and bis-(tri-o-tolylphosphine) palladium (II) chloride (1.65 g, 2.04 mmol). This mixture was heated to reflux for 3.5 hours and then cooled to ambient temperature for continued stirring overnight. The solvent was then removed under reduced pressure prior to dilution with EtOAc/water. The organic layer was extracted with additional EtOAc. The combined organics were washed with water, then brine. The organics were then dried over sodium sulfate, filtered, and then concentrated to obtain the crude product. This crude product was passed through a silica pad, eluting with 8:1 heptane:EtOAc to get 41.6 grams of methyl 4′-cyano-1,1′-biphenyl-2-carboxylate.

출처