p-Fluoronitrobenzene → 2-[2-(4-Nitrophenoxy)ethoxy]pyridine

HRID 2111798Notes

Reaction equation

HRID 2111798 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH2:10][CH2:11][OH:12].[H][H].[N+:15]([C:18]1[CH:23]=[CH:22][C:21](F)=[CH:20][CH:19]=1)([O-:17])=[O:16]>CN(C=O)C>[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([O:12][CH2:11][CH2:10][O:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=2)=[CH:20][CH:19]=1)([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 122163042-(2-Hydroxyethoxy)pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 690616702-[2-(4-Nitrophenoxy)ethoxy]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (21.6 mg, 0.90 mmol) in anhydrous DMF (0.5 mL), 2-(pyridin-2-yloxy)-ethanol (100 mg, 0.72 mmol) in DMF (1.5 mL) was added drop-wise under a N2 atmosphere. Once hydrogen gas evolution ceased, 4-nitrofluorobenzene (102 mg, 0.72 mmol, 76 μL) was added drop-wise to the yellow suspension. The resultant red-orange solution was allowed to stir at rt for 18 h. Upon completion, distilled water (2 mL) was added and the bright yellow solid precipitate was filtered, washed with distilled water, and dried in vacuo to give 2-[2-(4-nitrophenoxy)ethoxy]pyridine as a pale yellow solid. 1H NMR (d6-DMSO, 400 MHz): δ 8.21 (ddd, J=5.6, 3.6, 3.6 Hz, 2H), 7.72 (ddd, J=9.2, 7.2, 2.0 Hz, 1H), 7.21 (ddd, J=5.6, 3.6, 3.6 Hz, 1H), 7.01 (ddd, J=7.0, 4.8, 0.8 Hz, 1H), 6.86 (ddd, J=8.4, 0.8, 0.8 Hz, 1H), 4.62 (m, 2H), 4.49 (m, 2H). MS(ES+): m/z 261 [MH+].

Workup

  1. additionwas added drop-wise under a N2 atmosphere
  2. distillationUpon completion, distilled water (2 mL)
  3. additionwas added
  4. filtrationthe bright yellow solid precipitate was filtered
  5. washwashed with distilled water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-2653671b49d34717888c31c75097a5c8
Source dataset
uspto-grants-2009_04
Patent number
US07521448B2

Reaction notes

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