Potassium Iodide → 1-Bromo-4-chloro-2-iodobenzene

Temperature

0 °C

A suspension of 2-bromo-5-chlorobenzenamine (11.348 g, 54.963 mmol) in concentrated HCl (100 mL) was cooled to 0° C. and then treated in a dropwise fashion over 20 minutes using an addition funnel with a solution of sodium nitrite (4.5506 g, 65.955 mmol) in water (20 mL). The reaction was stirred at 0° C. for 75 minutes. A solution of potassium iodide (27.372 g, 164.89 mmol) in water (50 mL) was added, and the reaction was stirred at 23° C. After 1 hour, the reaction was heated to 70° C. After 18 hours, the reaction was diluted with EtOAc (500 mL) and washed with water (300 mL), 2N NaOH solution (300 mL), saturated sodium thiosulfate solution (300 mL), and brine (250 mL). The organic layer was dried over MgSO4, concentrated in vacuo, and purified by silica gel chromatography (eluant: hexane) affording 11.11 g of 1-bromo-4-chloro-2-iodobenzene.

1. additiontreated in a dropwise fashion over 20 minutes
2. stirringthe reaction was stirred at 23° C
3. waitAfter 1 hour
4. temperaturethe reaction was heated to 70° C
5. waitAfter 18 hours
6. washwashed with water (300 mL), 2N NaOH solution (300 mL), saturated sodium thiosulfate solution (300 mL), and brine (250 mL)
7. dry with materialThe organic layer was dried over MgSO4
8. concentrationconcentrated in vacuo
9. custompurified by silica gel chromatography (eluant: hexane)

ORD record

ord-eb6284e1bbec424c81e70daab2bf4c81

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07635715B2