Sodium hydride → HCID 19825428, compound

HRID 2249285Notes

Reaction equation

HRID 2249285 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[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20]Br)=[CH:16][CH:15]=1.[Cl-].[NH4+]>CN(C)C=O>[Br:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][O:9][CH2:20][C:17]2[CH:16]=[CH:15][C:14]([CH2:13][O:9][CH2:8][C:7]3[CH:10]=[CH:11][C:4]([Br:3])=[CH:5][CH:6]=3)=[CH:19][CH:18]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 693351,4-Bis(bromomethyl)benzeneHCID 701194-Bromobenzyl alcohol

Product 1

HCID 19825428HCID 19825428, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 951 mg (23.8 mmol) of sodium hydride contained at 60% in mineral oil in dry dimethylformamide (50 ml) was added 2.64 g (14.1mmol) of 4-bromobenzyl alcohol in an atmosphere of argon, and the mixture was allowed to react at 40°-50° C. for 30 min. Then, 1.62 g (6.14 mmol) of α,α'-dibromo-p-xylene was added, and the mixture was reacted at room temperature for 19 hours. To the reaction mixture at 0° C. was added a 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 (4:1) yielded 1.83 g (3.84 mmol) of 1,4-bis[3-(4-bromophenyl)-2-oxapropyl]benzene.

Workup

  1. customto react at 40°-50° C. for 30 min
  2. customthe mixture was reacted at room temperature for 19 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 (4:1)

Sources & evidence

ORD record
ord-d66008334c3a411ba4ecaabaa418e6cc
Source dataset
uspto-grants-1991_08
Patent number
US05043142

Reaction notes

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