Epichlorohydrin → 4-Benzyloxy-1-(2,3-epoxypropoxy)-2-fluorobenzene

HRID 5020Notes

Reaction equation

HRID 5020 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([F:16])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([CH:19]1[O:21][CH2:20]1)Cl.N1CCCCC1>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:17][CH:19]2[O:21][CH2:20]2)=[C:11]([F:16])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 7835EpichlorohydrinHCID 8082PiperidineHCID 13578007Phenol, 2-fluoro-4-(phenylmethoxy)-

Product 1

HCID 197975824-Benzyloxy-1-(2,3-epoxypropoxy)-2-fluorobenzene

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).

Workup

  1. customAfter removal of the volatile material, 40 ml tetrahydrofuran and 20 ml 2M NaOH
  2. additionis added
  3. customis evaporated
  4. customthe residue partitioned between methylenechloride and water
  5. customThe organic phase is purified over silica gel with toluene

Sources & evidence

ORD record
ord-3f1ba7546b9c42598686538126fd8e3a
Source dataset
uspto-grants-1993_09
Patent number
US05242943

Reaction notes

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