Reaction #1583832

Reaction equation

2-chloro-5-iodotoluene

N-bromosuccinimide

→

title compound

Yield 97.3%

2-(bromomethyl)-1-chloro-4-iodobenzene

Yield 97.3%

Solvents

dichloromethane

water

Conditions

Workup

1. 1
   OtherThe reaction mixture was irradiated with a halogen sun lamp (150 watt) for 2 h
2. 2
   OtherThe two-phase reaction mixture
3. 3
   Otherwas separated
4. 4
   Extractionthe aqueous layer was extracted with dichloromethane (50 mL)
5. 5
   WashThe combined organic layers were washed with water (2×150 mL)
6. 6
   Dryingdried over magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated under reduced pressure

Procedure

To a mixture of 2-chloro-5-iodotoluene (4.07 g, 16.12 mmol), N-bromosuccinimide (3.16 g, 17.73 mmol) in dichloromethane (258 mL) and water (258 mL) was added 2,2′-azodiisobutyronitrile (0.132 g, 0.81 mmol). The reaction mixture was irradiated with a halogen sun lamp (150 watt) for 2 h and then cooled to room temperature. The two-phase reaction mixture was separated, and the aqueous layer was extracted with dichloromethane (50 mL). The combined organic layers were washed with water (2×150 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure to provide the title compound as an orange oil (5.20 g).

Source