Hydrochloric Acid → 2,3,4-Trifluoro-5chlorobenzyl alcohol

Reaction equation

[BH4-].[Na+].[Cl:3][C:4]1[C:5]([F:15])=[C:6]([F:14])[C:7]([F:13])=[C:8]([CH:12]=1)[C:9](F)=[O:10].Cl>O1CCOCC1>[F:13][C:7]1[C:6]([F:14])=[C:5]([F:15])[C:4]([Cl:3])=[CH:12][C:8]=1[CH2:9][OH:10]

Participants

Procedure

62 g of NaBH4 are initially introduced into 320 ml of dioxane. A solution of 319 g of 5-chloro-2,3,4-trifluorobenzoyl fluoride in 640 ml of dioxane is run into this, at the reflux temperature, over the course of 6 hours. After boiling under reflux for a further hour, the mixture is poured onto ice, the pH is adjusted to 1 with dilute hydrochloric acid, and the organic phase is extracted with methylene chloride and then distilled: 261 g of 2,3,4-trifluoro-5-chlorobenzyl alcohol of boiling point 109° C./12 mbar are obtained.