Ammonium Hydroxide → 1,2-Difluoronaphthalene

Participants

Reaction Steps

A solution of the tetrafluoro naphthalene, 1,1,2,2-tetrafluoro-1,2-dihydronaphthalene (5.25 g , 25.66 mmol) in THF (15 ml) was treated with 30% aqueous NH4OH (30 ml) and zinc (8.45 g, 130 mmol) (powder) and stirred under N2 for 4 hours at RT. The reaction was monitored by GC/MS for disappearance of the starting material and found to be complete. The solution was filtered, extracted with hexane (30 ml), and filtered through a short silica column (20 g). The hexane solution was evaporated in vacuo to afford an oil. This crystallized on cooling to room temperature to afford 3.99 g (95% yield) of product. MS: m/e 164 (M+).

Provenance & Evidence