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

HRID 599630Notes

Reaction equation

HRID 599630 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-f55fcce351594dc1a9c5141b5b587d00
Source dataset
uspto-grants-2011_03
Patent number
US07897632B2

Reaction notes

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