Triethylamine → HCID 17748075, compound

Participants

Reaction Conditions

Reaction Steps

Ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide (8.5 g, 38.8 mmol) and 4-chloroiodoanisole (7.87 g, 33.0 mmol) was dissolved in N,N-dimethylformamide (65 ml). Palladium acetate (139 mg, 0.62 mmol) and triphenylphosphine (357 mg, 1.36 mmol) was added to the reaction followed by triethylamine (12.5 ml, 89.3 mmol). The reaction was flushed with nitrogen and heated at 140° C. for 16 hours. The reaction was cooled to room temperature and quenched with 1N HCl (250 ml). The aqueous solution was extracted with ethyl acetate (3×200 ml). The organic solution was dried over MgSO4, filtered and concentrated in vacuo to afford a solid. The solid was dissolved in dichloromethane and purified by dry flash chromatography (SiO2, heptane to 1:1 heptane: ethyl acetate). The fractions were combined to afford (E)-2-(4-chloro-phenyl)-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide (5.0 g, 46% yield).

Provenance & Evidence