Water → HCID 15205870, compound

Participants

Reaction Steps

To a solution of 2-bromoanisole (3.5 g, 18.7 mmol) in 40 mL of THF at -7° C. is added n-butyl lithium (11.7 mL of a 1.6 M solution in THF, 18.7 mmol). The solution is stirred for 15 minutes. After this time, ZnCl2 (20 mL of a 1 M solution in Et2O, 20 mmol) is added. The solution is allowed to warm to ambient temperature, and stirred for 3 hours. After this time, a solution of 4-iodobromobenzene (5.6 g, 19.8 mmol) and tetrakis(triphenylphosphine)-palladium(0) (1.1 g, 1 mmol) in 30 mL of THF is added. The reaction mixture is stirred for 16 hours. After this time, the solution is poured into 100 mL of H2O. The solution is diluted with EtOAc. The organic layer is washed with 2 N NH4OH, H2O and saturated NaCl. The organic layer is dried over MgSO4, filtered, and concentrated. The crude product is purified by column chromatography eluting with gradient of 10% CH2Cl2 /hexanes to 20% CH2Cl2 /hexanes to afford the title compound (2.61 g, 10 mmol) as a crystalline solid.

Provenance & Evidence