Benzyl Bromide → HCID 67085084, compound

HRID 2036743Notes

Reaction equation

HRID 2036743 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:12]([O:8][C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 139704965-Bromo-2-nitrophenol

Product 1

HCID 67085084HCID 67085084, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5-bromo-2-nitrophenol (10.4 g, 47.7 mmol), benzyl bromide (9.8 g, 57.2 mmol) and potassium carbonate (9.9 g, 71.5 mmol) was taken up in acetone (50 mL) and heated to reflux for 5 h. After cooling to ambient temperature, the reaction mixture was concentrated in vacuo, diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude material was purified by flash column chromatography (9:1 hexanes/ethyl acetate) to give 2-(benzyloxy)-4-bromo-1-nitrobenzene (14.19 g, 97%) as a light-yellow solid: 1H NMR (CDCl3, 300 MHz) δ 7.76 (d, J=8.4 Hz, 1H), 7.32-7.48 (m, 5H), 7.30 (d, J=1.8 Hz, 1H), 7.19 (dd, J=8.7, 1.8 Hz, 1H), 5.23 (s, 2H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 h
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. additiondiluted with water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by flash column chromatography (9:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-a0195e8ce954490196f9254c12596de8
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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