반응 #554238

반응 방정식

4-chlorophenethyl alcohol

triphenylphosphine

N-bromosuccinimide

→

4-chlorophenethyl bromide

수율 54.5%

용매

THF

THF

반응 조건

후처리

1. 1
   기타was evaporated
2. 2
   여과The solution was filtered
3. 3
   기타to remove triphenylphosphine oxide
4. 4
   기타the filtrate evaporated
5. 5
   workup.ADDITIONtreated with hexane
6. 6
   여과The stirred mixture was filtered
7. 7
   기타evaporated
8. 8
   workup.DISTILLATIONthe residue distilled under reduced pressure

실험 절차

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).

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