تفاعل #10166

معادلة التفاعل

water

potassium carbonate

methyl 2-iodobenzoate

4-cyano-phenylboronic acid

→

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

المردود 86.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThis mixture was heated
2. 2
   درجة الحرارةto reflux for 3.5 hours
3. 3
   أخرىThe solvent was then removed under reduced pressure
4. 4
   استخلاصThe organic layer was extracted with additional EtOAc
5. 5
   غسيلThe combined organics were washed with water
6. 6
   تجفيفThe organics were then dried over sodium sulfate
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated
9. 9
   أخرىto obtain the crude product
10. 10
    غسيلeluting with 8:1 heptane

الإجراء التجريبي

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.

المصدر