Reacción #464582

Ecuación de reacción

triisopropyl borate

6-methoxybenzo[b]thiophene

n-BuLi

→

6-methoxybenzo[b]thiophene-2-boronic acid

Rendimiento 71.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otropartitioned between 1.0 N HCl and EtOAc (300 mL each)
2. 2
   OtroThe layers were separated
3. 3
   Secadothe organic phase was dried over Na2SO4
4. 4
   ConcentraciónConcentration in vacuo
5. 5
   Otroproduced a white solid
6. 6
   Otrothat was triturated from Et2O/hexanes
7. 7
   FiltraciónFiltration

Procedimiento

To a solution of 6-methoxybenzo[b]thiophene (Graham, S. L., et al. J. Med. Chem. 1989, 32, 2548-2554)(18.13 g, 0.111 mol) in 150 mL of anhydrous THF at -60° C. was added n-BuLi (76.2 mL, 0.122 mol, 1.6 M solution in hexanes), dropwise via syringe. After stirring for 30 min, triisopropyl borate (28.2 mL, 0.122 mol) was introduced via syringe. The resulting mixture was allowed to gradually warm to 0° C. and then partitioned between 1.0 N HCl and EtOAc (300 mL each). The layers were separated, and the organic phase was dried over Na2SO4. Concentration in vacuo produced a white solid that was triturated from Et2O/hexanes. Filtration provided 16.4 g (71%) of 6-methoxybenzo[b]thiophene-2-boronic acid as a white solid.

Fuente