4-Fluoroaniline → 3-(4-Fluorophenylamino)propan-1-ol

HRID 2235761Notes

Reaction equation

HRID 2235761 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.F[B-](F)(F)F.[Li+].[O:15]1[CH2:18][CH2:17][CH2:16]1.C(=O)(O)[O-].[Na+]>C(#N)C>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:18][CH2:17][CH2:16][OH:15])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 97314-FluoroanilineHCID 10423OxetaneHCID 516892Sodium BicarbonateHCID 4298216Lithium tetrafluoroborate

Product 1

HCID 220132173-(4-Fluorophenylamino)propan-1-olYield 81.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-fluoroaniline (3.82 g) and lithium tetrafluoroborate (3.32 g) were added to a solution of oxetane (1.00 g) in acetonitrile (20 mL) at room temperature, and the reaction solution was stirred at room temperature for 64 hours. A saturated sodium bicarbonate solution was added to the reaction solution, followed by extraction with chloroform. The resulting extract was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 2.37 g of the title compound. The property values of the compound are as follows.

Workup

  1. extractionfollowed by extraction with chloroform
  2. extractionThe resulting extract
  3. dry with materialwas dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-6203e4f77b5e43fb824bfe776412f373
Source dataset
uspto-grants-2010_05
Patent number
US07713993B2

Reaction notes

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