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

HRID 895612Notes

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

Participants

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

stirringstirred at the same temperature for 3 hours
customthe layers were separated
extractionthe aqueous layer was extracted with dichloromethane (10 ml)
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
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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