4-Fluoroaniline → N-(2,2-dimethoxyethyl)-4-fluoroaniline

HRID 2067308Notes

Reaction equation

HRID 2067308 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH3:9][O:10][CH:11]([O:14][CH3:15])[CH:12]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.[Cl-].[Na+].O>[CH3:9][O:10][CH:11]([O:14][CH3:15])[CH2:12][NH:6][C:5]1[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 97314-FluoroanilineHCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 63686639N-(2,2-dimethoxyethyl)-4-fluoroanilineYield 57%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 4-fluoroaniline (2.00 mL, 21.1 mmol) and dimethoxyacetaldehyde (60% solution in water, 3.30 mL, 21.9 mmol) in tetrahydrofuran (100 mL) was added sodium triacetoxyborohydride (6.70 g, 30.0 mmol) at ambient temperature. The resulting reaction mixture was stirred at ambient temperature for 12 hours, followed by the addition of brine (50 mL) then extraction with ethyl acetate (3×100 mL). The combined organic solution was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo, and the residue was purified by column chromatography to afford N-(2,2-dimethoxyethyl)-4-fluoroaniline (2.30 g, 57%): MS (ES+) m/z 200.6 (M+1).

Workup

  1. customThe resulting reaction mixture
  2. extractionextraction with ethyl acetate (3×100 mL)
  3. dry with materialThe combined organic solution was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b1ee369ed61b4e4795a074d28467124c
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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