Tert-butyl(4-chloro-2-ethynylphenoxy)acetate → Tert-butyl(4-chloro-2-{[2-fluoro-5-(propylsulfonyl)phenyl]ethynyl}phenoxy)acetate

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-1-fluoro-4-(propylsulfonyl)benzene (Intermediate 106; 541 mg; 1.93 mmol), tert-butyl(4-chloro-2-ethynylphenoxy)acetate (Intermediate 467 mg; 1.75 mmol), dichlorobis(triphenylphosphine)palladium(II) (49 mg; 0.07 mmol) and TEA (728 μL; 5.2 mmol) was heated at 60° C. for 18 hours. The reaction mixture was taken up in EtOAc, washed twice with a sat. NH4Cl aqueous solution and once with brine. The organic phase was dried over MgSO4, filtered and concentrated to dryness affording a crude, which was purified by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc. The title compound was obtained as a brown solid.

Provenance & Evidence