Réaction #67260

Équation de réaction

5-bromo-2-hydroxybenzaldehyde

epibromohydrin

K2CO3

water

→

title compound

Rendement 95.7%

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

Rendement 95.7%

Solvants

DMF

EtOAc

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was cooled to ambient temperature
2. 2
   AutreThe phases were separated
3. 3
   Lavagethe combined organic phases were washed with brine
4. 4
   Séchagedried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   AutreThe residue was purified by flash column chromatography (isooctane/EtOAc)

Mode opératoire

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).

Source