Potassium Carbonate → HCID 13078523, compound

HRID 2164628Notes

Reaction equation

HRID 2164628 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH3:10][S:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>O.CN(C)P(N(C)C)(N(C)C)=O>[CH3:10][S:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 140864-(Methylthio)phenolHCID 145174-FluorobenzonitrileHCID 14798Sodium Hydroxide

Product 1

HCID 13078523HCID 13078523, compoundYield 46.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 12.1 g (0.100 mole) of 4-fluorobenzonitrile, 21.0 g (0.150 mole) of 4-(methylthio)phenol, 20.7 g (0.150 mole) of anhydrous potassium carbonate (K2CO3) and 150 ml of hexamethyl phosphoramide was heated at 100° C. for 4 hrs. The reaction mixture was cooled and poured into a solution of 200 ml of 20% aqueous NaOH and 500 ml of water. The crystalline product was collected by filtration and washed well with water. The product was dissolved in CH2Cl2 and dried (Na2SO4). Removal of solvent in vacuo afforded 11.3 g (46.9% yield) of product. Recrystallization from hexane gave purified 4-(4-(methylthio)phenoxy)benzonitrile, mp 65°-66° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationThe crystalline product was collected by filtration
  3. washwashed well with water
  4. dissolutionThe product was dissolved in CH2Cl2
  5. dry with materialdried (Na2SO4)
  6. customRemoval of solvent in vacuo

Sources & evidence

ORD record
ord-51bd997e71ff419591e3b1d410c12255
Source dataset
uspto-grants-1985_03
Patent number
US04505929

Reaction notes

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