Reaction #67260

Reaction equation

5-bromo-2-hydroxybenzaldehyde

epibromohydrin

K2CO3

water

→

title compound

Yield 95.7%

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

Yield 95.7%

Solvents

DMF

EtOAc

Conditions

Workup

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

Procedure

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