Methyl trifluoroacetate → 2,2,2-Trifluoro-1-(4-vinylphenyl)ethanone

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Reaction Steps

The (4-vinylphenyl)magnesium bromide solution of Example 1 was cooled to −78° C. using a dry ice /acetone bath and a solution of methyl trifluoroacetate (20.00 g, 156.19 mmol) in THF (25 mL) was added dropwise over 15 min. The reaction mixture was stirred in the cooling bath for 1 h, then quenched by pouring into cold 1N H2SO4. The aqueous solution was extracted with ether and the combined extracts were washed with brine, dried (Na2SO4), and concentrated to provide 17.81 g of a pale yellow oil. This material was purified by vacuum distillation to provide 12.65 g (46%) of a colorless oil: bp 59-60° C. (1.4 mm); 1H NMR (CDCl3) δ 8.05 (d, 2ArH), 7.55 (d, 2ArH), 6.79 (dd, CH═), 5.97 (dd, ═CHH), 5.51 (dd ═CHH).

Provenance & Evidence