Reacción #67260

Ecuación de reacción

5-bromo-2-hydroxybenzaldehyde

epibromohydrin

K2CO3

water

→

title compound

Rendimiento 95.7%

5-BROMO-2-(OXIRAN-2-YLMETHOXY)BENZALDEHYDE

Rendimiento 95.7%

Disolventes

DMF

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was cooled to ambient temperature
2. 2
   OtroThe phases were separated
3. 3
   Lavadothe combined organic phases were washed with brine
4. 4
   Secadodried (Na2SO4)
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe residue was purified by flash column chromatography (isooctane/EtOAc)

Procedimiento

A mixture of 5-bromo-2-hydroxybenzaldehyde (10 g, 50 mmol), epibromohydrin (13.6 g, 100 mmol) and K2CO3 (10.3 g, 75 mmol) in DMF (50 ml) was heated at 60° C. for 2 h. The mixture was cooled to ambient temperature and water and EtOAc was added. The phases were separated and the combined organic phases were washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by flash column chromatography (isooctane/EtOAc) to give the title compound (12.3 g). MS m/z (rel. intensity, 70 eV) 256 (M+, 41), 201 (77), 200 (bp), 199 (84), 63 (60).

Fuente