N-bromobutanimide → 2-(Bromomethyl)-1-chloro-4-iodobenzene

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).

1. customThe reaction mixture was irradiated with a halogen sun lamp (150 watt) for 2 h
2. customThe two-phase reaction mixture
3. customwas separated
4. extractionthe aqueous layer was extracted with dichloromethane (50 mL)
5. washThe combined organic layers were washed with water (2×150 mL)
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-b862707337964a4b86f36c2f868d1800

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822521B2