Réaction #1596948

Équation de réaction

4-bromo-5-ethyl-2-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]tetrahydropyran

hydrogen

triethylamine

→

5-ethyl-2-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]tetrahydropyran

Solvants

toluene water

Conditions de réaction

Traitement

1. 1
   AutreThe organic phase is separated off
2. 2
   Filtrationfiltered absorptively (SiO2, toluene)
3. 3
   ConcentrationThe filtrate is concentrated to dryness
4. 4
   Autrethe residue is recrystallised from ethanol at reduced temperature

Mode opératoire

18.0 g (36.2 mmol) of 4-bromo-5-ethyl-2-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]tetrahydropyran are hydrogenated for 30 h at a hydrogen pressure of 5 bar and at 80° C. in toluene/water in the presence of Pd/C (5% of Pd) and 12.7 ml (88.1 mmol) of triethylamine. The organic phase is separated off and filtered absorptively (SiO2, toluene). The filtrate is concentrated to dryness, and the residue is recrystallised from ethanol at reduced temperature, giving 5-ethyl-2-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]tetrahydropyran as a colourless solid.

Source