Reacción #73801

Ecuación de reacción

4-Chlorophenylmagnesium bromide

4-bromobenzaldehyde

Water

→

title compound

(4-Bromo-phenyl)-(4-chloro-phenyl)-methanol

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solvent was removed under reduced pressure
2. 2
   OtroThe residue was then partitioned between ethyl acetate and 1N HCl solution
3. 3
   LavadoThe organic layer was washed with brine
4. 4
   Secadodried (MgSO4)
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe crude product was then purified by column chromatography (SiO2)
8. 8
   Lavadoeluting with ethyl acetate/petroleum ether (1:9)

Procedimiento

4-Chlorophenylmagnesium bromide (12.97 ml, 1M solution in diethyl ether) was added slowly to a solution of 4-bromobenzaldehyde (2.0 g, 10.81 mmol) in tetrahydrofuran (25 ml) at 0° C., under an atmosphere of nitrogen. The reaction mixture was allowed to warm to room temperature and was stirred for 17 hours. Water (3 ml) was then added and the solvent was removed under reduced pressure. The residue was then partitioned between ethyl acetate and 1N HCl solution. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated. The crude product was then purified by column chromatography (SiO2), eluting with ethyl acetate/petroleum ether (1:9), to yield the title compound (2.30 g). LC/MS: (PS-B3) Rt 3.49 [M−H]+ 297.

Fuente