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

HRID 963651

Reaction equation

HRID 963651 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-78f9cef888a24e68a2a625d65ec2517c
Source dataset
uspto-grants-1998_06
Patent number
US05763615

Linked notes

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