Reaction #40266

Reaction equation

N-chlorosuccinimide

6-bromo-2-naphthol

→

6-bromo-1-chloro-2-naphthol

Yield 95.4%

Solvents

dichloromethane

Conditions

Workup

1. 1
   OtherThe synthesis of (S1-2)
2. 2
   TemperatureThe reaction solution was heated to room temperature
3. 3
   Washwashed with saturated sodium bicarbonate solution and water
4. 4
   Dryingdried over magnesium sulfate
5. 5
   workup.DISTILLATIONdistilled under a reduced pressure
6. 6
   Otherto remove the solvent
7. 7
   OtherRecrystallization

Procedure

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