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

HRID 880472Notes

Reaction equation

HRID 880472 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[OH:19].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:19][C:11]1[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:10]=1[Cl:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 692642-Chloro-5-nitrophenol

Product 1

HCID 128819332-(Benzyloxy)-1-chloro-4-nitrobenzeneYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzyl bromide (0.6 mL, 5.04 mmol) was added dropwise to a mixture of 2-chloro-5-nitro-phenol (800 mg, 4.61 mmol) and potassium carbonate (1.27 g, 9.22 mmol) in acetone (20 mL) at ambient temperature and then heated at reflux for 2 h. The inorganic residue was filtered off and washed with acetone (20 mL). The combined filtrate and washings were concentrated in vacuo and the resulting residue was then dissolved in ethyl acetate (25 mL) and washed successively with water (2×20 mL), brine (20 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to yield 2-benzyloxy-1-chloro-4-nitro-benzene (1.20 g, 99%) as a cream solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 h
  3. filtrationThe inorganic residue was filtered off
  4. washwashed with acetone (20 mL)
  5. concentrationThe combined filtrate and washings were concentrated in vacuo
  6. dissolutionthe resulting residue was then dissolved in ethyl acetate (25 mL)
  7. washwashed successively with water (2×20 mL), brine (20 mL)
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7ed985d7eef045f3b58459196320a00d
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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