4-BROMO-3-IODOANISOLE

i) l-Bromo-2-iodo-4-methoxy-benzene Bromine (2.8 mL, 54.49 mmol) was added dropwise over 5 minutes to a solution of 3- iodoanisole (10.01 g, 42.77 mmol) in glacial acetic acid (65 mL). The resulting orange solution was stirred at room temperature for 24 hours. The reaction mixture was diluted with water and extracted with hexane. The combined extracts were washed with aqueous sodium thiosulfate solution (5percent) and brine, dried over magnesium sulfate and concentrated under reduced pressure to give 13.51 g (quantitative yield) of the title compound. To a round bottomed flask (100mL) containing a magnetic stirrer and 7 3-iodoanisole (3) (2.0g, 8.5mmol) in 54 DMF (20mL) was added 8 N-bromosuccinimide (1.54g, 8.67mmol). The reaction mixture was heated to 80°C and stirred at this temperature for 6h. After cooling to room temperature, the mixture was quenched with the saturated aqueous NaCl solution (100mL), 6N aqueous solution of 62 HCl (10mL), and extracted with EtOAc (50mL×3).The combined organic extracts were dried over anhydrous MgSOStep A:

Molecular Weight:312.93
XLogP3:3.2
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:311.86467
Monoisotopic Mass:311.86467
Topological Polar Surface Area:9.2
Heavy Atom Count:10
Complexity:110
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes