Reaktion #80079

Reaktionsgleichung

(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

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched by the addition of dilute aqueous NaHCO3
2. 2
   ExtraktionThe resulting mixture was extracted with Et2O
3. 3
   Waschenthe combined organic layers were washed with H2O and saturated aqueous NaCl
4. 4
   Trocknenbefore being dried (Na2SO4)
5. 5
   Einengenconcentrated under reduced pressure

Vorschrift

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.

Quelle