Benzyl Bromide → 3-(Benzyloxy)-4-nitrobenzaldehyde

HRID 660546Notes

Reaction equation

HRID 660546 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[CH:13]=[O:14].C(=O)([O-])[O-].[K+].[K+]>O>[CH2:1]([O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[CH:13]=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 697123-Hydroxy-4-nitrobenzaldehyde

Product 1

HCID 121117193-(Benzyloxy)-4-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of benzyl bromide (6.9 g, 40.3 mmol) and 3-hydroxy-4-nitrobenzaldehyde (9.7 g, 58.0 mmol) is added potassium carbonate (8.9 g, 64.4 mmol). The mixture is stirred at RT for 18 h, diluted with water and extracted with EtOAc. The organic phase is washed with aqueous potassium carbonate and brine, dried over MgSO4, filtered and concentrated to afford the title compound as a yellow solid: (M+1)+=258.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase is washed with aqueous potassium carbonate and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-265a3e5aca85443aa0f1480bbc71275d
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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