Ethyl 4-pentenoate → Ethyl 2-(4-bromo-2-chlorobenzyl)pent-4-enoate

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Reaction Steps

Add LDA (5.27 mL, 10.5 mmol, 2.0 M) into a solution of ethyl pent-4-enoate (0.9 g, 7.0 mmol), in THF (125 mL) at −78° C. and stir for 15 minutes. Add 4-bromo-2-chlorobenzyl bromide (3.3 g, 10.5 mmol) and warm reaction to room temperature. Quench with ammonium chloride solution, extract the reaction mixture with methylene chloride and wash the organic layer with brine. Dry over sodium sulfate, filter and concentrate. Purify the residue with silica gel column (hexanes) to afford the title compound (1.65 g, 73%) as colorless oil.

Provenance & Evidence