Reaktion #554238

Reaktionsgleichung

4-chlorophenethyl alcohol

triphenylphosphine

N-bromosuccinimide

→

4-chlorophenethyl bromide

Ausbeute 54.5%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas evaporated
2. 2
   FiltrationThe solution was filtered
3. 3
   Sonstigeto remove triphenylphosphine oxide
4. 4
   Sonstigethe filtrate evaporated
5. 5
   workup.ADDITIONtreated with hexane
6. 6
   FiltrationThe stirred mixture was filtered
7. 7
   Sonstigeevaporated
8. 8
   workup.DISTILLATIONthe residue distilled under reduced pressure

Vorschrift

A stirred solution of 4-chlorophenethyl alcohol (131 g) and triphenylphosphine (241.3 g) in dry THF (500 mL) at 0° C. was treated portionwise over 30 min. with N-bromosuccinimide (163.75 g). The resulting black solution was stirred overnight at room temperature, whereupon the THF was evaporated and the residue stirred with ether. The solution was filtered to remove triphenylphosphine oxide and the filtrate evaporated and treated with hexane. The stirred mixture was filtered, evaporated, and the residue distilled under reduced pressure to give 100 g of 4-chlorophenethyl bromide as a colorless liquid, b.p. 85° C. (3 mm Hg).

Quelle