Benzyl Bromide → Benzyl 3-benzyloxy-2-nitrobenzoate

HRID 506530Notes

Reaction equation

HRID 506530 reaction equation
[OH:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:14]([O:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH2:5][C:4]1[CH:8]=[CH:9][CH:10]=[CH:2][CH:3]=1)=[O:6])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2932913-Hydroxy-2-nitrobenzoic acid

Product 1

HCID 10594871Benzyl 3-benzyloxy-2-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Hydroxy-2-nitrobenzoic acid (10.5 g) was dissolved in 60 ml of N,N-dimethylformamide, then 15 ml of benzyl bromide and 19.0 g of potassium carbonate were added at 0° C. and the mixture was stirred at room temperature for one night. The reaction solution was filtered through Celite and the filtrate was concentrated in vacuo. Water was added to the resulting residue, the mixture was extracted with ether and the extract was washed with a saturated saline and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo to give 20.7 g of benzyl 3-benzyloxy-2-nitrobenzoate.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionWater was added to the resulting residue
  4. extractionthe mixture was extracted with ether
  5. washthe extract was washed with a saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-9e3f33102db64eef96edaf1f9dd001b9
Source dataset
uspto-grants-2010_08
Patent number
US07786106B2

Reaction notes

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