Hydrochloric Acid → 2-(3-Fluoro-4-methylphenyl)benzonitrile

HRID 234758Notes

Reaction equation

HRID 234758 reaction equation
CC1(C)O[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([F:20])[CH:14]=2)=[N:4]C1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)=O.Cl>CCOCC>[F:20][C:15]1[CH:14]=[C:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:5]#[N:4])[CH:18]=[CH:17][C:16]=1[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 545155994,5-Dihydro-5,5-dimethyl-2-(3'-fluoro-4'-methyl-biphenyl-2-yl)oxazole

Product 1

HCID 542386242-(3-Fluoro-4-methylphenyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

97.0 g (343 mmol) of the compound from Example III are initially introduced into 500 ml of pyridine, and 31.3 ml (343 mmol) of phosphorus oxychloride are added at 0° C., while stirring. The mixture is heated slowly, and is finally boiled under reflux for 1 hour. After cooling to room temperature, ether and an amount of 1M hydrochloric acid such that the pH of the aqueous phase is 1.5 are added. The organic phase is washed three more times with 1M sulphuric acid, dried with sodium sulphate and evaporated on a rotary evaporator and the residue is freed from the residual solvent under a high vacuum.

Workup

  1. additionare added at 0° C.
  2. temperatureThe mixture is heated slowly
  3. temperatureunder reflux for 1 hour
  4. additionare added
  5. washThe organic phase is washed three more times with 1M sulphuric acid
  6. dry with materialdried with sodium sulphate
  7. customevaporated on a rotary evaporator

Sources & evidence

ORD record
ord-03a275f73cc44f37bf751a999adad78a
Source dataset
uspto-grants-1997_01
Patent number
US05596006

Reaction notes

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