تفاعل #167943

معادلة التفاعل

4-bromo-2-hydroxybenzonitrile

potassium cyclopropyltrifluoroborate

K3PO4

→

4-cyclopropyl-2-hydroxybenzonitrile

المذيبات

toluene

EtOAc NH4Cl

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was then cooled to room temperature
2. 2
   ترشيحfiltered through a pad of Celite
3. 3
   أخرىThe organic layer was seperated
4. 4
   تجفيفdried over Na2SO4
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated
7. 7
   أخرىThe residue was purified by FCC (0-50% EtOAc/heptane)

الإجراء التجريبي

A solution of 4-bromo-2-hydroxybenzonitrile (1 g, 5.05 mmol), potassium cyclopropyltrifluoroborate (1.495 g, 10.10 mmol), K3PO4 (5.05 ml, 15.15 mmol) and PdCl2(Amphos)2 (0.358 g, 0.505 mmol) in toluene (25 mL) was allowed to stir at 100° C. under nitrogen overnight. The mixture was then cooled to room temperature, diluted with EtOAc/NH4Cl(aq), and filtered through a pad of Celite. The organic layer was seperated, dried over Na2SO4, filtered and concentrated. The residue was purified by FCC (0-50% EtOAc/heptane) to provide 4-cyclopropyl-2-hydroxybenzonitrile, 1H NMR (400 MHz, CH2Cl2) δ 12.17 (br. s., 1H), 7.23 (d, J=8.34 Hz, 1H), 6.51-6.58 (m, 2H), 1.82 (tt, J=5.02, 8.37 Hz, 1H), 0.94-1.00 (m, 2H), 0.68-0.73 (m, 2H).

المصدر