Reaction #43586

Reaction equation

3-fluoro-4,5-dihydroxybenzaldehyde

potassium carbonate

1,2-dibromoethane

→

desired compound

Yield 95.4%

8-fluoro-2,3-dihydro-1,4-benzodioxin-6-carboxaldehyde

Yield 95.4%

Solvents

DMF

Conditions

Workup

1. 1
   Otherwas removed under reduced pressure
2. 2
   workup.ADDITIONThe reaction mixture was then treated with dichloromethane and water
3. 3
   ExtractionThe aqueous phase was extracted twice with dichloromethane
4. 4
   Otherthe combined organic phases were dried
5. 5
   Otherthe solvent was removed under reduced pressure

Procedure

To a solution of 3-fluoro-4,5-dihydroxybenzaldehyde (0.66 g, 4.2 mmol) in DMF (30 ml) was added potassium carbonate (1.15 g, 8.3 mmol) and 1,2-dibromoethane (0.72 ml, 8.3 mmol) and the resultant mixture was heated to 80° C. for 18 h before the solvent was removed under reduced pressure. The reaction mixture was then treated with dichloromethane and water. The aqueous phase was extracted twice with dichloromethane and the combined organic phases were dried and the solvent was removed under reduced pressure to give the desired compound as a cream solid (0.73 g, 95%).

Source