Sodium hydride → HCID 19825389, compound

HRID 2249276Notes

Reaction equation

HRID 2249276 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([OH:15])[CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12].[Br:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1.[Cl-].[NH4+]>CN(C)C=O>[CH3:14][O:13][C:9]1[CH:8]=[C:7]([O:15][CH2:21][C:20]2[CH:23]=[CH:24][C:17]([Br:16])=[CH:18][CH:19]=2)[CH:6]=[C:5]([O:4][CH3:3])[C:10]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 685274-Bromobenzyl bromideHCID 695053,4,5-Trimethoxyphenol

Product 1

HCID 19825389HCID 19825389, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.46 g (36.5 mmol) of sodium hydride contained at 60% in mineral oil in dry dimethylformamide (50 ml) was added 2.02 g (11.0 mmol) of 3,4,5-trimethoxyphenol in an atmosphere of argon, and the mixture was allowed to react at 0° C. for 15 min. To the reaction mixture was added 3.60 g (14.4 mmol) of 4-bromobenzyl bromide. The resulting mixture was reacted at room temperature for 24 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 (1:1) yielded 3.28 g (9.28 mmol) of 4-bromobenzyl 3,4,5-trimethoxyphenyl ether.

Workup

  1. customto react at 0° C. for 15 min
  2. customThe resulting mixture was reacted at room temperature for 24 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-2d6e217948444a908d79315c7ddf47a6
Source dataset
uspto-grants-1991_08
Patent number
US05043142

Reaction notes

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