反応 #73801

反応方程式

4-Chlorophenylmagnesium bromide

4-bromobenzaldehyde

Water

→

title compound

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

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   その他the solvent was removed under reduced pressure
2. 2
   その他The residue was then partitioned between ethyl acetate and 1N HCl solution
3. 3
   洗浄The organic layer was washed with brine
4. 4
   乾燥dried (MgSO4)
5. 5
   ろ過filtered
6. 6
   濃縮concentrated
7. 7
   その他The crude product was then purified by column chromatography (SiO2)
8. 8
   洗浄eluting with ethyl acetate/petroleum ether (1:9)

実験手順

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.

出典