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Water → 1-Bromo-3-[2-(4-diethylcarbamoylbenzyl)phenoxy]propane

HRID 895612
Notes
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Reaction equation

HRID 895612 reaction equation
[CH2:1]([N:3]([CH2:20][CH3:21])[C:4]([C:6]1[CH:19]=[CH:18][C:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])=[CH:8][CH:7]=1)=[O:5])[CH3:2].[H-].[Na+].[Br:24][CH2:25][CH2:26][CH2:27]Br.O>O1CCCC1>[Br:24][CH2:25][CH2:26][CH2:27][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH2:10][C:9]1[CH:18]=[CH:19][C:6]([C:4](=[O:5])[N:3]([CH2:1][CH3:2])[CH2:20][CH3:21])=[CH:7][CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 223807182-(4-Diethylcarbamoylbenzyl)phenol

Product 1

HCID 120503951-Bromo-3-[2-(4-diethylcarbamoylbenzyl)phenoxy]propaneYield 69%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
60 °C

Procedure

2-(4-Diethylcarbamoylbenzyl)phenol (100 mg) was dissolved in tetrahydrofuran (2 ml), added with sodium hydride (60%, in oil, 21 mg) and stirred at 60° C. for 1.5 hours. The reaction mixture was added with 1,3-dibromopropane (0.18 ml) and stirred at the same temperature for 3 hours. After the reaction mixture was added with water (10 ml) and the layers were separated, the aqueous layer was extracted with dichloromethane (10 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=3:1) to obtain 99 mg of the title compound. Yield: 69%.

Workup

  1. stirringstirred at the same temperature for 3 hours
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted with dichloromethane (10 ml)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-799802a6badc43e7b58bc9bab0040e96
Source dataset
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06916822B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes