Benzyl Bromide → HCID 54325576, compound

HRID 747801Notes

Reaction equation

HRID 747801 reaction equation
[C:1]([CH2:4][CH2:5][C:6]([N+:17]([O-:19])=[O:18])([CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH2:7][CH2:8][C:9]([OH:11])=[O:10])([OH:3])=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(#N)C>[CH2:26]([O:10][C:9]([CH2:8][CH2:7][C:6]([CH2:5][CH2:4][C:1]([O:3][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:2])([N+:17]([O-:19])=[O:18])[CH2:12][CH2:13][C:14]([O:16][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:15])=[O:11])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 28016004-(2-Carboxyethyl)-4-nitroheptanedioic acid

Product 1

HCID 54325576HCID 54325576, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of [3-(2-carboxyethyl)]-3-nitropentane-1,5-dicarboxylic acid (2.8 g, 0.01 mole) (prepared as described by James K. Young et al., Macromolecules, 1994, 27, 3464-34-71) and cesium carbonate (3.25 g, 0.025 mol) in acetonitrile (20.0 mL) was added benzylbromide (8.55 g, 6.0 mL, 0.05 mole) and the mixture stirred at RT for 24 h. Inorganic salts were filtered and the salts washed with acetonitrile. The filtrate and the washings were combined and evaporated to obtain an oil. Purification by chromatography over silica gel (hexane:ethyl acetate, 7:3) afforded the benzyl ester (40) as colorless viscous oil (4.5 g, yield: 82%). Mass Spectrum (M+H)+=548.

Workup

  1. filtrationInorganic salts were filtered
  2. washthe salts washed with acetonitrile
  3. customevaporated
  4. customto obtain an oil
  5. customPurification by chromatography over silica gel (hexane:ethyl acetate, 7:3)

Sources & evidence

ORD record
ord-83cd79d957c3452485737d34374e8fe8
Source dataset
uspto-grants-2008_07
Patent number
US07399460B2

Reaction notes

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