Réaction #40266

Équation de réaction

N-chlorosuccinimide

6-bromo-2-naphthol

→

6-bromo-1-chloro-2-naphthol

Rendement 95.4%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   AutreThe synthesis of (S1-2)
2. 2
   TempératureThe reaction solution was heated to room temperature
3. 3
   Lavagewashed with saturated sodium bicarbonate solution and water
4. 4
   Séchagedried over magnesium sulfate
5. 5
   workup.DISTILLATIONdistilled under a reduced pressure
6. 6
   Autreto remove the solvent
7. 7
   AutreRecrystallization

Mode opératoire

The synthesis of (S1-2) was carried out following the method described in Synlett, No. 18, 2837 (2005), wherein 29.9 g of N-chlorosuccinimide and 600 ml of dichloromethane were added to a reactor in nitrogen atmosphere and cooled to 0° C., 2.6 g of zirconium (IV) chloride was added, and then 50 g of 6-bromo-2-naphthol (S1-1) was added slowly. The reaction solution was heated to room temperature and stirred for 10 hours, then washed with saturated sodium bicarbonate solution and water, dried over magnesium sulfate, and distilled under a reduced pressure to remove the solvent. Recrystallization was carried out using a mixed solvent of toluene/heptane=1/1 (volumetric ratio) to obtain 55 g of 6-bromo-1-chloro-2-naphthol (S1-2).

Source