Reacción #159775

Ecuación de reacción

4-benzyl-6-bromo-spiro[3H-1,4-benzoxazine-2,1′-cyclopropane]

n-BuLi

5-bromo-2-chlorobenzaldehyde

→

(4-benzylspiro[3H-1,4-benzoxazine-2,1′-cyclopropane]-6-yl)-(5-bromo-2-chloro-phenyl)methanol

Rendimiento 49.4%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGAfter stirring for 1 h
2. 2
   Otrothe reaction was quenched by the addition of saturated ammonium chloride solution
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   LavadoThe ethyl acetate layer was washed with water, brine
5. 5
   Secadodried over sodium sulphate
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe resulting residue was purified by silica gel column chromatography

Procedimiento

To a stirred solution of 4-benzyl-6-bromo-spiro[3H-1,4-benzoxazine-2,1′-cyclopropane] (1.12 g, 3.4 mmol) in THF (10 mL) was added 1.6 M solution of n-BuLi in hexanes (2.12 mL, 3.4 mmol) at −78° C. The reaction mixture was stirred for 30 min, and then transferred to a stirred solution of 5-bromo-2-chlorobenzaldehyde (745 mg, 3.4 mmol) in THF (10 mL) at −78° C. After stirring for 1 h, the reaction was quenched by the addition of saturated ammonium chloride solution and extracted with ethyl acetate. The ethyl acetate layer was washed with water, brine, dried over sodium sulphate, and concentrated. The resulting residue was purified by silica gel column chromatography to furnish (4-benzylspiro[3H-1,4-benzoxazine-2,1′-cyclopropane]-6-yl)-(5-bromo-2-chloro-phenyl)methanol (790 mg).

Fuente