تفاعل #746281

معادلة التفاعل

carbon tetrabromide

n-butyllithium

N,N-dimethylethanolamine

2-Phenylpyridine

→

title compound

2-Bromo-6-phenyl-pyridine

المذيبات

Water

heptane

heptane

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe reaction mixture stirred for a further 1 hour
2. 2
   درجة الحرارةThe reaction was then cooled
3. 3
   workup.WAITThe reaction was kept at −78° C. for 1 hour
4. 4
   درجة الحرارةto warm to ambient temperature
5. 5
   استخلاصextracted with TBME (×2)
6. 6
   تجفيفdried (Na2SO4)
7. 7
   تركيزthe solvent concentrated in vacuo
8. 8
   أخرىThe crude product was purified by column chromatography
9. 9
   غسيلeluting with 5% EtOAc in heptane

الإجراء التجريبي

To N,N-dimethylethanolamine (0.8 mL, 8.00 mmol) in heptane (10 mL) cooled externally to 0° C. was added dropwise a 2.5 M n-butyllithium solution (6.40 mL) and the reaction mixture stirred for 30 minutes. 2-Phenylpyridine (12) (412 mg, 2.66 mmol) in heptane (5 mL) was then added and the reaction mixture stirred for a further 1 hour. The reaction was then cooled and carbon tetrabromide (3.18 g, 9.60 mmol) was added whilst maintaining the temperature at −78° C. The reaction was kept at −78° C. for 1 hour and then allowed to warm to ambient temperature. Water was cautiously added and extracted with TBME (×2), dried (Na2SO4) and the solvent concentrated in vacuo. The crude product was purified by column chromatography eluting with 5% EtOAc in heptane to give the title compound. Yield: 300 mg, 48%; LC-MS tr 1.63 min; HPLC Purity: 97%; MS (ES+) m/z 234, 236 (M+H)

المصدر