7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-one → 7-bromo-4-fluoro-2-methoxy-9-vinyl-9H-xanthen-9-ol

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Reaction Steps

To a solution of vinylmagnesium chloride (55.9 ml, 89.4 mmol) at −78° C. was added dropwise of a solution of 7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-one (8.0 g, 24.76 mmol) in THF (99 mL). After 30 min, the reaction was allowed to slowly warm to rt, then quenched with 240 mL of saturated aqueous NH4Cl. The mixture was extracted with EtOAc. The organic layer was dried over magnesium sulfate, filtered and concentrated to yield 7-bromo-4-fluoro-2-methoxy-9-vinyl-9H-xanthen-9-ol (8.69 g, 24.76 mmol, 100% yield) as yellow solid.

Provenance & Evidence