Sodium borohydride → 8-Chloro-3,7-difluoro-10-hydroxy-10,11-dihydrodibenzo(b,f)thiepine

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Reaction Steps

A solution of sodium borohydride (1.0 g) in water (3 ml) containing 2 drops of 20% sodium hydroxide solution was added dropwise to a stirred solution of the ketone from the preceding experiment (7.9 g) in dioxane (100 ml). The mixture was refluxed for 6 hours, the dioxane evaporated in vacuo and the residue mixed with water and extracted with benzene. Evaporation of the extract and crystallization of the residue from an ether-cyclohexane mixture yielded 6.0 g of the pure 8-chloro-3,7-difluoro-10-hydroxy-10,11-dihydrodibenzo(b,f)thiepine, m.p. 84°-86° C.

Provenance & Evidence