反応 #80079

反応方程式

(4-bromo-2-methyl-phenyl)-methanol

Intermediate 133

(4-bromo-2-methyl-phenyl)-methanol

triphenylphosphine

N-bromosuccinimide

→

title compound

4-Bromo-1-bromomethyl-2-methyl-benzene

溶媒

CH2Cl2

反応条件

後処理

1. 1
   その他The reaction was quenched by the addition of dilute aqueous NaHCO3
2. 2
   抽出The resulting mixture was extracted with Et2O
3. 3
   洗浄the combined organic layers were washed with H2O and saturated aqueous NaCl
4. 4
   乾燥before being dried (Na2SO4)
5. 5
   濃縮concentrated under reduced pressure

実験手順

A solution of (4-bromo-2-methyl-phenyl)-methanol (Intermediate 133, 319.0 mg, 1.58 mmol) and triphenylphosphine (466.0 mg, 1.74 mmol) in 5 mL CH2Cl2 was cooled to 0° C. and N-bromosuccinimide (309.0 mg, 1.74 mmol) was added in 5 portions over 20 minutes. The solution was warmed to 25° C. and stirred for 17 hours. The reaction was quenched by the addition of dilute aqueous NaHCO3. The resulting mixture was extracted with Et2O and the combined organic layers were washed with H2O and saturated aqueous NaCl before being dried (Na2SO4) and concentrated under reduced pressure. The title compound, 350.0 mg (84%), was isolated by column chromatography (2-3% EtOAc-hexanes) as a colorless oil.

出典