Sodium hydride → HCID 57260895, compound

HRID 2249288Notes

Reaction equation

HRID 2249288 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[C:6]([Cl:12])[CH:5]=1.[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[C:16]([Cl:22])[CH:15]=1.[Cl-].[NH4+]>CN(C)C=O>[Br:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][O:9][CH2:18][C:17]2[CH:20]=[CH:21][C:14]([Br:13])=[CH:15][C:16]=2[Cl:22])=[C:6]([Cl:12])[CH:5]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 219144864-Bromo-1-(bromomethyl)-2-chlorobenzeneHCID 43805739(4-Bromo-2-chlorophenyl)methanol

Product 1

HCID 57260895HCID 57260895, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 271 mg (6.78 mmol) of sodium hydride contained at 60% in mineral oil in dry dimethylformamide (25 ml) was added 1.00 g (4.52 mmol) of 4-bromo-2-chlorobenzyl alcohol in an atmosphere of argon, and the mixture was allowed to react at 40°-50° C. for 30 min. Then, 1.54 g (5.42 mmol) of 4-bromo-2-chlorobenzyl bromide was added, and the mixture was reacted at room temperature for 18 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 ethyl acetate-hexane (1:4) yielded 1.69 g (3.97 mmol) of bis(4-bromo-2-chlorobenzyl) ether.

Workup

  1. customto react at 40°-50° C. for 30 min
  2. customthe mixture was reacted at room temperature for 18 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 ethyl acetate-hexane (1:4)

Sources & evidence

ORD record
ord-e0f5131d0fc84dc69fea09a15e6d1136
Source dataset
uspto-grants-1991_08
Patent number
US05043142

Reaction notes

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