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

HRID 1109996

Reaction equation

HRID 1109996 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[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>[Cl:1][C:2]1[CH:3]=[C:4]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 102833-Chloro-4-nitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 8198614-(Benzyloxy)-2-chloro-1-nitrobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-chloro-4-nitrophenol (10 g, 0.058 mole), benzyl bromide (11.8 g, 0.069 mole), and potassium carbonate (16 g, 0.116 mole) in acetone is stirred, heated at reflux temperature for 17 hours, cooled and filtered. The filtrate is concentrated in vacuo to give a solid residue which is recrystallized from absolute ethanol to give the title compound, mp 82°-84.5° C., identified by elemental and NMR analyses.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 17 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated in vacuo
  6. customto give a solid residue which
  7. customis recrystallized from absolute ethanol

Sources & evidence

ORD record
ord-f89a0f77bb17487ca27e8667cc139775
Source dataset
uspto-grants-1994_06
Patent number
US05324711

Linked notes

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