Sodium hydride → HCID 19825432, compound

HRID 2249275Notes

Reaction equation

HRID 2249275 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1.[N+:12]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1)([O-:14])=[O:13].[Cl-].[NH4+]>CN(C)C=O>[N+:12]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19][O:9][CH2:8][C:7]2[CH:10]=[CH:11][C:4]([Br:3])=[CH:5][CH:6]=2)=[CH:17][CH:16]=1)([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 660114-Nitrobenzyl bromideHCID 701194-Bromobenzyl alcohol

Product 1

HCID 19825432HCID 19825432, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 812 mg (20.3 mmol) of sodium hydride contained at 60% in mineral oil in dry dimethylformamide (100 ml) was added 3.01 g (16.1 mmol) of 4-bromobenzyl alcohol in the atmosphere of argon, and the mixture was allowed to react at 40°-50° C. for 30 min. followed by addition of 2.85 g (13.2 mmol) of 4-nitrobenzyl bromide. The mixture was reacted at room temperature for 17 hours. To the reaction mixture at 0° C. was added saturated aqueous solution of ammonium chloride followed by extraction with ethyl acetate. The organic layer was washed with water and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography for separation and purification. Elution with dichloromethane-hexane (1:1) yielded 2.76 g (8.57 mmol) of 4-bromobenzyl 4-nitrobenzyl ether.

Workup

  1. customto react at 40°-50° C. for 30 min.
  2. customThe mixture was reacted at room temperature for 17 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water
  5. concentrationconcentrated under reduced pressure
  6. customThe residue thus obtained
  7. customwas subjected to silica gel column chromatography for separation and purification
  8. washElution with dichloromethane-hexane (1:1)

Sources & evidence

ORD record
ord-99a0a17268ce42a0814be1cb7600e7cb
Source dataset
uspto-grants-1991_08
Patent number
US05043142

Reaction notes

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