1,3-Propanediol → 3-(4-Fluoro-2-nitrophenoxy)propanol

HRID 345528Notes

Reaction equation

HRID 345528 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].[H-].[Na+].F[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17]>CN(C)C=O>[F:15][C:12]1[CH:13]=[CH:14][C:9]([O:4][CH2:3][CH2:2][CH2:1][OH:5])=[C:10]([N+:16]([O-:18])=[O:17])[CH:11]=1

Participants

5

Reactant 3

HCID 104421,3-PropanediolHCID 24758Sodium hydrideHCID 677672,5-Difluoronitrobenzene

Product 1

HCID 150969923-(4-Fluoro-2-nitrophenoxy)propanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 30.4 parts of 1,3-propanediol and 90 parts of N,N-dimethylformamide were added 5.28 parts of a sodium hydride dispersion 50% at a temperature below 20° C. Stirring was continued for 2 hours at room temperature under nitrogen atmosphere. Then there were added dropwise 15.9 parts of 1,4-difluoro-2-nitrobenzene so that the temperature had been maintained below 30° C. Upon completion, stirring was continued overnight at room temperature. The reaction mixture was poured onto water and the product was extracted with trichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column-chromatography over silica gel using trichloromethane as eluent. The pure fractions were collected and the eluent was evaporated, yielding 21.5 parts 3-(4-fluoro-2-nitrophenoxy)propanol as a residue (intermediate 24).

Workup

  1. temperaturehad been maintained below 30° C
  2. stirringUpon completion, stirring
  3. waitwas continued overnight at room temperature
  4. additionThe reaction mixture was poured onto water
  5. extractionthe product was extracted with trichloromethane
  6. washThe extract was washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by column-chromatography over silica gel
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated

Sources & evidence

ORD record
ord-ed137816dbf84c3d89eca587636cb00e
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

Loading…