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

HRID 1794708Notes

Reaction equation

HRID 1794708 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, 2 H), 7.17(d, J=9.1 Hz, 1 H), 7.30–7.55(m, 8 H), 7.60–7.70(m, 1 H), 7.80(d, J=2.9 Hz, 1 H), 8.15–8.25(m, 2 H); 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-f73204d80b954fc9b99cf5b4e21e88ff
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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