Benzyl Bromide → 2-(Benzyloxy)-1-bromo-3-nitrobenzene

HRID 1055684Notes

Reaction equation

HRID 1055684 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[OH:11].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[CH2:12]([O:11][C:3]1[C:4]([N+:8]([O-:10])=[O:9])=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 135454532-Bromo-6-nitrophenol

Product 1

HCID 218735142-(Benzyloxy)-1-bromo-3-nitrobenzene

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5.22 g (23.9 mmol) of 2-bromo-6-nitrophenol, 3.0 ml (25.1 mmol) of benzyl bromide and 3.64 g (26.3 mmol) of potassium carbonate in 50 ml of acetonitrile was heated under reflux for 2 h. After cooling to RT, the solid was filtered off and the filtrate was freed from the solvent on a rotary evaporator. The residue obtained was dissolved in ethyl acetate and washed successively with water and saturated sodium chloride solution. After drying over anhydrous magnesium sulphate, the mixture was filtered and the filtrate was concentrated on a rotary evaporator. The residue that remained was dried under high vacuum. This gave 7.53 g (99% of theory) of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. filtrationthe solid was filtered off
  4. customthe filtrate was freed from the solvent on a rotary evaporator
  5. customThe residue obtained
  6. washwashed successively with water and saturated sodium chloride solution
  7. dry with materialAfter drying over anhydrous magnesium sulphate
  8. filtrationthe mixture was filtered
  9. concentrationthe filtrate was concentrated on a rotary evaporator
  10. customThe residue that remained was dried under high vacuum

Sources & evidence

ORD record
ord-0573ad9fc49d4c0a9f10e34b35c68a58
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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