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

HRID 560535Notes

Reaction equation

HRID 560535 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-1ba4446c1a5c4507a4d0159f86254d49
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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