Sodium Hydroxide → HCID 68718410, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 9.0 g (30.1 mmol) of 2-bromo-1,5-di-tert-butyl-3-methoxybenzene (Zhang, H.; Kwong, F. Y.; Tian, Y.; Chan, K. S. J. Org. Chem. 1998, 63, 6886-6890) in 100 mL of DME was purged with nitrogen for 15 min and 1.5 g (0.13 mmol) of tetrakis(triphenylphosphine)palladium(0) was added. After stirring 20 min 5.0 g (31.9 mmol) of 4-chlorobenzeneboronic acid was added. The reaction mixture was stirred at 75° C. and 15 mL of 5 N sodium hydroxide was added dropwise. The resulting mixture was then stirred overnight at 80° C. The reaction mixture was then cooled to room temperature and the DME was removed in vacuo. The residue was partitioned between water and hexane containing 10% EtOAc and extracted. The organic layer was dried, filtered and evaporated to afford the title compound suitable for use in the next step.

Provenance & Evidence