Reacción #86195

Ecuación de reacción

Diisopropylamine

N-Butyllithium

Hexane

2-bromo-6-fluoro-pyridine

Paraformaldehyde

→

(6-bromo-2-fluoro-3-pyridyl)methanol

Rendimiento 36.1%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to −78° C
2. 2
   workup.STIRRINGThe mixture was stirred at −78° C. for 2.5 h
3. 3
   Temperaturato warm to room temperature
4. 4
   workup.STIRRINGstirred overnight
5. 5
   OtroThe reaction was quenched with water
6. 6
   OtroThe layers were separated
7. 7
   ExtracciónThe aqueous layer was extracted with EtOAc
8. 8
   ConcentraciónThe combined organic layers were concentrated
9. 9
   Otrothe residue was purified on silica
10. 10
    Lavadoeluted with 0 to 50% EtOAc in Heptane

Procedimiento

To Diisopropylamine (22.001 mmol; 2240 mg; 3.13 mL) in THF (40 mL) at 0° C. was added N-Butyllithium (2.5 mol/L) in Hexane (24.001 mmol; 9.6 mL). The reaction was stirred at 0° C. for 0.5 h, and then cooled to −78° C. 2-bromo-6-fluoro-pyridine (20.001 mmol; 3520.0 mg) in THF (10 mL) was added dropwise. The mixture was stirred at −78° C. for 2.5 h. Paraformaldehyde (40.002 mmol; 3603.3 mg) was added rapidly. The mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched with water. The layers were separated. The aqueous layer was extracted with EtOAc. The combined organic layers were concentrated and the residue was purified on silica eluted with 0 to 50% EtOAc in Heptane to afford (6-bromo-2-fluoro-3-pyridyl)methanol (1.4888 g, 36%).

Fuente