Reaction #5116

Reaction equation

4-benzyloxy-2-fluorophenol

epichlorhydrin

piperidine

→

4-benzyloxy-1-(2,3-epoxypropoxy)-2-fluorobenzene

Conditions

Workup

1. 1
   OtherAfter removal of the volatile material, 40 ml tetrahydrofuran and 20 ml 2M NaOH
2. 2
   workup.ADDITIONis added
3. 3
   Otheris evaporated
4. 4
   Otherthe residue partitioned between methylenechloride and water
5. 5
   OtherThe organic phase is purified over silica gel with toluene

Procedure

4.0 g of 4-benzyloxy-2-fluorophenol is reacted with 10 g epichlorhydrin and 0.2 ml piperidine for 90 minutes at 100°. After removal of the volatile material, 40 ml tetrahydrofuran and 20 ml 2M NaOH is added. After 1 hour stirring the solvent is evaporated and the residue partitioned between methylenechloride and water. The organic phase is purified over silica gel with toluene giving 4-benzyloxy-1-(2,3-epoxypropoxy)-2-fluorobenzene (colourless oil).

Source