3,3,3-Triethoxyprop-1-yne → 1-Bromo-4-chloro-2-(3,3,3-triethoxyprop-1-ynyl)benzene

Participants

Reaction Steps

A mixture of 1-bromo-4-chloro-2-iodobenzene (10 g, 32 mmol) in 100 mL degassed ACN and TEA (29 g, 284 mmol), was treated with 3,3,3-triethoxyprop-1-yne (6.0 g, 35 mmol), copper(I) iodide (0.60 g, 3.2 mmol), and dichlorobis(triphenylphosphine)palladium(II) (1.1 g, 1.6 mmol). The mixture was stirred at room temperature for 2 hours at room temperature (the mixture turned dark green after 5 minutes). TLC showed that all starting material was converted, and a new spot was produced. The mixture was concentrated in vacuo. The residue was diluted with 100 mL ether, washed with H2O (2×20 mL), 5% ammonia water (2×20 mL), brine (20 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was purified by column chromatography pretreated with TEA and eluted with 0-15% EtOAc/hexane to give 7.6 g of the product as a pale yellow oil. The oil solidified after it was stored in the refrigerator.

Provenance & Evidence