Sodium hydride → HCID 19825391, compound

HRID 2249277Notes

Reaction equation

HRID 2249277 reaction equation
[CH2:1]([OH:14])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH3:13].[H-].[Na+].Br[CH2:18][C:19]1[CH:20]=[C:21]([Br:27])[CH:22]=[CH:23][C:24]=1[CH2:25]Br.[Cl-].[NH4+]>CN(C)C=O>[CH2:18]([C:19]1[CH:20]=[C:21]([Br:27])[CH:22]=[CH:23][C:24]=1[CH2:25][O:14][CH2:1][CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH3:13])[O:14][CH2:1][CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH3:13]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 90263Tetraethylene glycol monomethyl etherHCID 124964654-Bromo-1,2-bis(bromomethyl)benzene

Product 1

HCID 19825391HCID 19825391, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Next, 3.74 g (18.0 mmol) of 3,6,9,12-tetraoxa-1-tridecanol was added to a solution of 1.92 g (48.0 mmol) of sodium hydride contained at 60% in mineral oil in dry dimethylformamide (65 ml) in the atmosphere of argon, and the mixture was allowed to react at 40°-50° C. for 30 min. Then, to the reaction mixture was added 2.57 g (7.49 mmol) of 3,4-bis(bromomethyl)-1-bromobenzene, 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 yielded 3.08 g (5.16 mmol) of 3,4-bis(2,5,8,11,14-pentaoxapentadecanyl)-1-bromobenzene.

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

Sources & evidence

ORD record
ord-d8cf0a134bf9440c94a89875d05bff62
Source dataset
uspto-grants-1991_08
Patent number
US05043142

Reaction notes

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