toluene-4-sulfonic acid (S)-2-(3-bromophenyl)-2-fluoro-ethyl ester → 1-bromo-(S)-3-(1-fluoropent-4-en-1-yl)benzene

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Reaction Steps

A solution of toluene-4-sulfonic acid (S)-2-(3-bromophenyl)-2-fluoro-ethyl ester (5 mmol) in THF at room temperature is treated dropwise with a 1M solution of allylmagnesium bromide, stirred at room temperature for 5 h, quenched with saturated NH4Cl and extracted with ethyl acetate. The extracts are combined, washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo to afford 1-bromo-(S)-3-(1-fluoropent-4-en-1-yl)benzene.

Provenance & Evidence