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

HRID 1966485Notes

Reaction equation

HRID 1966485 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(C)=O>[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-nitrobenzeneYield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-bromo-2-nitrophenol (5.2 g, 23.8 mmol) in acetone (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 4-bromo-2-nitro-1-[phenylmethyl)oxy]benzene (6 g), 92% yield. 1H NMR (500 MHz, CDCl3): δ 5.26 (s, 2H), 7.05 (d, J=8.9 Hz, 1H), 7.42 (m, 5H), 7.63 (dd, J=2.5 Hz, 1H), 8.01 (d, J=2.45 Hz, 1H). 13C NMR (500 MHz, CDCl3): δ 71.6, 112.4, 116.9, 127.1, 128.5, 128.6, 128.9, 135.2, 136.9, 140.7, 151.2.

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
  10. customto afford 4-bromo-2-nitro-1-[phenylmethyl)oxy]benzene (6 g), 92% yield

Sources & evidence

ORD record
ord-9782a3f61f954ea2aa23b7ebb7ee3370
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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