Sodium hydride → HCID 18520400, compound

HRID 1368781Notes

Reaction equation

HRID 1368781 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][OH:5].[H-].[Na+].F[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19]>CN(C=O)C>[F:17][C:14]1[CH:15]=[CH:16][C:11]([O:5][CH2:4][CH:3]([O:6][CH3:7])[O:2][CH3:1])=[C:12]([N+:18]([O-:20])=[O:19])[CH:13]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 677672,5-DifluoronitrobenzeneHCID 5423812,2-Dimethoxyethanol

Product 1

HCID 18520400HCID 18520400, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A DMF solution (50 ml) of 16.7 g of 2,2-dimethoxyethanol was added to dry DMF (60 ml) suspension of 4.32 g of sodium hydride at room temperature over 20 minutes. After 1 hour of stirring at room temperature, the reaction solution was cooled to 0° C., mixed with a DMF (20 ml) solution of 23.9 g of 2,5-difluoronitrobenzene and then stirred at 0° C. for 1 hour. The reaction solution was poured into 700 ml of ice water and extracted twice with a hexane-ethyl acetate (9:1) mixed solvent. The organic layer was washed with water and saturated brine in that order and dried with anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure to obtain 35.88 g of the title compound as a light red oil.

Workup

  1. temperaturethe reaction solution was cooled to 0° C.
  2. stirringstirred at 0° C. for 1 hour
  3. extractionextracted twice with a hexane-ethyl acetate (9:1)
  4. additionmixed solvent
  5. washThe organic layer was washed with water and saturated brine in that order
  6. dry with materialdried with anhydrous sodium sulfate
  7. customthe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-8e19e2f39caf4657a76b317fd1c890af
Source dataset
uspto-grants-2003_06
Patent number
US06573377B1

Reaction notes

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