Reacción #682949

Ecuación de reacción

6-Bromo-2-chloro-3-iodopyridine

2-(benzyloxy)acetaldehyde

NH4Cl

→

2-(benzyloxy)-1-(6-bromo-2-chloropyridin-3-yl)ethanol

Rendimiento 95.4%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONfollowed by addition of isopropylmagnesium chloride-lithium chloride complex (3.99 mL, 5.18 mmol)
2. 2
   Temperaturathe resulting mixture warmed to 0° C.
3. 3
   workup.STIRRINGstirred for 2 h
4. 4
   Extracciónextracted with ethyl acetate
5. 5
   LavadoThe organic layer was washed with brine
6. 6
   Secadodried (Na2SO4)
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated in vacuo

Procedimiento

6-Bromo-2-chloro-3-iodopyridine (1.50 g, 4.71 mmol) was dissolved in THF (15 mL) and cooled to −78° C., followed by addition of isopropylmagnesium chloride-lithium chloride complex (3.99 mL, 5.18 mmol). The mixture was stirred at −78° C. for 1 h. 2-(benzyloxy)acetaldehyde (0.849 g, 5.65 mmol) was added and the resulting mixture warmed to 0° C. and stirred for 2 h. The mixture was treated with saturated NH4Cl and extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to gave 2-(benzyloxy)-1-(6-bromo-2-chloropyridin-3-yl)ethanol (1.54 g, yield: 95%). MS (M+H)+: 344.

Fuente