Epichlorohydrin → HCID 20212125, compound

HRID 1906519Notes

Reaction equation

HRID 1906519 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[OH:12].[H-].[Na+].[CH2:15]([CH:17]1[O:19][CH2:18]1)Cl>CN(C=O)C>[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:10])([F:11])[F:9])=[CH:4][C:3]=1[O:12][CH2:15][CH:17]1[CH2:18][O:19]1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 24758Sodium hydrideHCID 138235382-Iodo-5-(trifluoromethyl)phenol

Product 1

HCID 20212125HCID 20212125, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A sample of 20 g (0.069 mole) of 2-iodo-5-trifluoromethylphenol was added in portions to a suspension of 0.07 mole of NaH (from 3.36 g of 50% NaH which had been washed free of oil with hexane) in 150 ml of dry DMF under N2. When gas evolution had ceased, a 27 ml (0.347 mole) sample of epichlorohydrin was added dropwise at 5° C. The mixture was heated at 60° C. for 3 hr and allowed to stand at 25° C. for 16 hr. A precipitate was removed by filtration. The filtrate was concentrated to dryness in vacuo. The residue was taken up in ether, washed with water and brine, dried (K2CO3) and the solvent evaporated in vacuo to give 20.4 g (86% yield) of [(2-iodo-5-trifluoromethylphenoxy)methyl]oxirane as an oil.

Workup

  1. customA precipitate was removed by filtration
  2. concentrationThe filtrate was concentrated to dryness in vacuo
  3. washwashed with water and brine
  4. dry with materialdried (K2CO3)
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-91cbc5e5b04a4ed185c800e5fcaa4970
Source dataset
uspto-grants-1987_03
Patent number
US04652584

Reaction notes

Loading…