Hexane → 1-(Bromomethyl)-2-chloro-4-iodobenzene

Temperature

55 °C

To a solution of 2-chloro-4-iodotoluene (7.59 g) in carbon tetrachloride (76 ml) were added N-bromosuccinimide (5.89 g) and 2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile) (Wako V-70, 281 mg) at room temperature and the mixture was stirred at 55° C. for 3.5 hr. The reaction mixture was allowed to cool to room temperature and thereto was added hexane (76 ml). Insoluble matter was filtered off. The filtrate was concentrated and the residue was again dissolved in hexane. The mixture washed successively with water, 5% aqueous sodium thiosulfate solution, saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated to give 2-chloro-4-iodobenzyl bromide (8.45 g) as an oil.

1. temperatureto cool to room temperature
2. filtrationInsoluble matter was filtered off
3. concentrationThe filtrate was concentrated
4. dissolutionthe residue was again dissolved in hexane
5. washThe mixture washed successively with water, 5% aqueous sodium thiosulfate solution, saturated aqueous sodium hydrogencarbonate solution and saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. customThe solvent was evaporated

ORD record

ord-d0fc97d3f12948978589290299bce05a

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07060721B1