Benzyl Bromide → 1-(Benzyloxy)-4-bromo-2-nitrobenzene

HRID 130427

Reaction equation

HRID 130427 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(=O)CC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 243644-Bromo-2-nitrophenol

Product 1

HCID 112782421-(Benzyloxy)-4-bromo-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 4-bromo-2-nitrophenol (5.2 g, 23.8 mmol) in 2-butanone (100 ml) was added potassium carbonate (9.0 g, 65.1 mmol) followed by benzyl bromide (2.6 ml, 21.8 mmol). The resulting mixture was stirred at room temperature for 30 minutes and then heated to reflux overnight. The solids were then removed by filtration, washing with acetone, and the filtrate reduced in vacuo. The residue was dissolved in ethyl acetate and washed with 2M aqueous sodium hydroxide solution (×3) and then brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered and reduced in vacuo to afford the title product. 1H-NMR (d6-DMSO) δ 8.14 (1H, d, J 3.5 Hz), 7.84 (1H, dd, J 11.0, 3.5 Hz), 7.45-7.39 (5H, m), 7.37-7.33 (2H, m), 5.32 (2H, s).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. customThe solids were then removed by filtration
  4. washwashing with acetone
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with 2M aqueous sodium hydroxide solution (×3)
  7. customThe organic layer was separated
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered

Sources & evidence

ORD record
ord-54d0e43941364bf29defb0d7fa95d4b9
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Linked notes

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