Benzyl Bromide → 1,3-Dibenzyl 5-nitrobenzene-1,3-dicarboxylate

HRID 889840Notes

Reaction equation

HRID 889840 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]([OH:15])=[O:14])[CH:7]=[C:8]([C:10]([OH:12])=[O:11])[CH:9]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C>[CH2:22]([O:14][C:13](=[O:15])[C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=[C:8]([C:10]([O:12][CH2:13][C:6]2[CH:7]=[CH:8][CH:9]=[CH:4][CH:5]=2)=[O:11])[CH:7]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 120695-Nitroisophthalic acid

Product 1

HCID 190639261,3-Dibenzyl 5-nitrobenzene-1,3-dicarboxylateYield 76.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (60 mL) was stirred 5-nitro-1,3-benzenedicarboxylic acid (2.1 g, 10 mmol) and potassium carbonate (8.3 g, 60 mmol). To this was added benzyl bromide (3.60 g, 21 mmol) and the mixture stirred at room temperature for 18 hours. The mixture was then filtered free of solids and the DMF solution evaporated at reduced pressure to give an oil. The oil was partitioned between methylene chloride (100 mL) and 10% citric acid solution (100 mL). The organic phase was separated, washed successively with saturated sodium bicarbonate solution (100 mL) and then brine (100 mL). The organic phase was dried over magnesium sulfate and evaporated at reduced pressure to give 1.5 g (39%) of the solid diester. MS: M-benzyl=300.1.

Workup

  1. filtrationThe mixture was then filtered free of solids
  2. customthe DMF solution evaporated at reduced pressure
  3. customto give an oil
  4. customThe oil was partitioned between methylene chloride (100 mL) and 10% citric acid solution (100 mL)
  5. customThe organic phase was separated
  6. washwashed successively with saturated sodium bicarbonate solution (100 mL)
  7. dry with materialThe organic phase was dried over magnesium sulfate
  8. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-3d7a494e1f5c49418735167d948cc434
Source dataset
uspto-grants-2006_02
Patent number
US06995151B2

Reaction notes

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