Benzyl Bromide → Benzoic acid 4-benzyloxy-3-nitro-phenyl ester

HRID 1061205Notes

Reaction equation

HRID 1061205 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:20]([O:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 11097269HCID 11097269, compound

Product 1

HCID 53642911Benzoic acid 4-benzyloxy-3-nitro-phenyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of benzoic acid 4-hydroxy-3-nitro-phenyl ester (Tapia, R.; Torres, G. and Valderrama, J. A. Synth. Commun. 1986, 16, 681) (20.7 g, 80 mmol), benzyl bromide (42.75 g, 250 mmol), potassium carbonate (48.3 g, 350 mmol) and DMF (300 mL) was stirred at room temperature for 2 days. After removing the solvent the residue was dissolved in water and extracted with CH2Cl2. The organic extracts were dried (MgSO4) and concentrated. The product was purified by flash silica gel chromatography eluting with CH2Cl2 to give the title compound as a pale yellowish solid (25.1 g, 90%); 1H NMR (300 MHz, CDCl3) δ 5.27(s, 2H), 7.17 (d, J=9.1 Hz, 1H), 7.30-7.55 (m, 8H), 7.60-7.70 (m, 1H), 7.80 (d, J=2.9 Hz, 1H), 8.15-8.25 (m, 2H); MS (ES) m/z: 345.0 (MH+, 100%); HRMS Calcd. for C20H15NO5 (M+): 349.0951. Found: 349.0952.

Workup

  1. customAfter removing the solvent the residue
  2. dissolutionwas dissolved in water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic extracts were dried (MgSO4)
  5. concentrationconcentrated
  6. customThe product was purified by flash silica gel chromatography
  7. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-cc2548d0b4b64bf186c36e4e754bdcb4
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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