Benzene, 1-chloro-4-fluoro- → 4-Chlorophenyl phenyl ether

HRID 1703435Notes

Reaction equation

HRID 1703435 reaction equation
[O-:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K+].F[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1>CN1CCCC1=O.O>[CH:5]1[CH:6]=[CH:7][C:2]([O:1][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 9604Benzene, 1-chloro-4-fluoro-HCID 23670670Potassium phenoxide

Product 1

HCID 234364-Chlorophenyl phenyl etherYield 54.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A stirred solution containing 14.8 g (0.112 mole) of potassium phenoxide and 13.1 g (0.10 mole) of p-fluorochlorobenzene in 100 ml of N-methyl-2-pyrrolidinone is heated at reflux for a period of time necessary to effect complete reaction, as determined by vapor phase chromotography techniques. The crude reaction mixture is cooled and diluted to a volume of 400 ml with water, whereupon it is extracted with several portions of ether. The combined organic extracts are washed with a 5% sodium hydroxide solution, water, and a saturated sodium chloride solution, dried (magnesium sulfate), and concentrated in vacuo. Distillation at reduced pressure affords 11.1 g (54%) of material, b(0.05 mm) 73.5°-75.5°, whose spectral properties are in agreement with the desired structure.

Workup

  1. temperatureis heated
  2. temperatureat reflux for a period of time necessary
  3. customreaction
  4. customThe crude reaction mixture
  5. temperatureis cooled
  6. extractionis extracted with several portions of ether
  7. washThe combined organic extracts are washed with a 5% sodium hydroxide solution, water
  8. dry with materiala saturated sodium chloride solution, dried (magnesium sulfate)
  9. concentrationconcentrated in vacuo
  10. distillationDistillation at reduced pressure

Sources & evidence

ORD record
ord-b3412459b0ec4907a094e0e03353d75c
Source dataset
uspto-grants-1978_11
Patent number
US04124370

Reaction notes

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