4-Fluorobenzyl bromide → 5-(4-Fluoro-benzyl)-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone

참여 물질

반응 조건

반응 단계

To a solution of 3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (200 mg, 0.86 mmol) in THF (3 ml) under N2 at −78° C. is added, dropwise, a 1.8 M solution of lithium diisopropylamine in tetrahydrofuran/heptane/ethylbenzene (0.53 ml, 0.95 mmol). The resulting solution is allowed to stir at −78° C. for 40 minutes. A solution of 4-fluorobenzyl bromide (0.16 ml, 1.3 mmol) in THF (1 ml) is then added in one portion, the reaction mixture is stirred at −78° C. for 30 minutes before being allowed to warm to room temperature over a period of 60 minutes. The reaction is quenched by the addition of saturated aqueous ammonium chloride (5 ml) and extracted with ethyl acetate (2×10 ml). The combined organics are purified by flash chromatography to give 5-(4-fluoro-benzyl)-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (236 mg).

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