Sodium hydride → HCID 12548636, compound

HRID 2249281Notes

Reaction equation

HRID 2249281 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1.[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1>CN(C)C=O>[Br:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][O:9][CH2:17][C:16]2[CH:19]=[CH:20][C:13]([Br:12])=[CH:14][CH:15]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromideHCID 701194-Bromobenzyl alcohol

Product 1

HCID 12548636HCID 12548636, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 27.4 g (685 mmol) of sodium hydride contained at 60% in mineral oil in dry dimethylformamide (425 ml) was added 42.4 g (227 mmol) of 4-bromobenzyl alcohol in an atmosphere of argon, and the mixture was allowed to react at 40-50° C. for 30 min. Then, 62.4 g (250 mmol) of 4-bromobenzyl bromide was added, and the mixture was reacted at room temperature for 15 hours. The reaction mixture was added to ice water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and 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 72.7 g (204 mmol) of 4-bromobenzyl ether.

Workup

  1. customto react at 40-50° C. for 30 min
  2. customthe mixture was reacted at room temperature for 15 hours
  3. extractionthe mixture was extracted 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-b4d10a18ba1248e5bb27daa5beae706e
Source dataset
uspto-grants-1991_08
Patent number
US05043142

Reaction notes

Loading…