4-Fluorobenzyl chloride → 5-(4-Fluoro-benzyloxy)-2-nitro-meta-xylene

HRID 453940Notes

Reaction equation

HRID 453940 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[C:6]([CH3:11])[C:7]=1[N+:8]([O-:10])=[O:9].[F:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][O:12][C:4]2[CH:5]=[C:6]([CH3:11])[C:7]([N+:8]([O-:10])=[O:9])=[C:2]([CH3:1])[CH:3]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 96024-Fluorobenzyl chlorideHCID 11430Potassium CarbonateHCID 1384663,5-Dimethyl-4-nitrophenol

Product 1

HCID 670834645-(4-Fluoro-benzyloxy)-2-nitro-meta-xylene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3,5-dimethyl-4-nitrophenol (0.97 g, 5.79 mmol), 4-fluorobenzyl chloride (1.26 g, 8.69 mmol) and anhydrous potassium carbonate (1.24 g, 9.0 mmol) in 50 ml of acetone was stirred under reflux for 22 hours. TLC showed this reaction is complete. The reaction mixture was cooled to room temperature and filtered and washed with acetone. The filtrate was evaporated to dryness to give the crude product, which was used for next step without further purification.

Workup

  1. temperatureunder reflux for 22 hours
  2. filtrationfiltered
  3. washwashed with acetone
  4. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-a6ac003ef0014afa89d6ce38f6a7d273
Source dataset
uspto-grants-2013_07
Patent number
US08492588B2

Reaction notes

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