Reaction #73801

Reaction equation

4-Chlorophenylmagnesium bromide

4-bromobenzaldehyde

Water

→

title compound

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

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Otherthe solvent was removed under reduced pressure
2. 2
   OtherThe residue was then partitioned between ethyl acetate and 1N HCl solution
3. 3
   WashThe organic layer was washed with brine
4. 4
   Dryingdried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   OtherThe crude product was then purified by column chromatography (SiO2)
8. 8
   Washeluting with ethyl acetate/petroleum ether (1:9)

Procedure

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.

Source