Tributylphosphine → (6-(4-Bromo-7-fluoroindan-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid methyl ester

Participants

Reaction Steps

Reaction under argon atmosphere: to a solution of 15.3 g (66.3 mmol) of 4-bromo-7-fluoroindan-1-ol (product of step 1) and 11.0 g (53.0 mmol) of (6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetic acid methyl ester in 60.0 ml DCM are added 29.7 ml (116 mmol) of tributylphosphine. 24.4 ml (116 mmol) of diisopropylazodicarboxylate are added dropwise and under cooling in an ice/EtOH bath at 5° C.-15° C. over 20 min. It is stirred at r.t. for 1 h. The solvent is evaporated and the residue is chromatographed on silica gel (PE/EtOAc=100/0→95/5) to give the title compound. Yield: 16.9 g; LC (method 4): tR=4.84 min; Mass spectrum (ESI+): m/z=421 [M+H]+.

Provenance & Evidence