3-Methoxyphenol → 3-Chloro-2-p-methoxyphenoxy-5-trifluoromethylpyridine

HRID 1650909Notes

Reaction equation

HRID 1650909 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7](O)[CH:6]=[CH:5][CH:4]=1.[H-].[Na+].ClC1[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][N:14]=1.[C:24](=O)([O-])[O-:25].[K+].[K+]>CS(C)=O.O>[Cl:19][C:18]1[C:1]([O:2][C:3]2[CH:8]=[CH:7][C:6]([O:25][CH3:24])=[CH:5][CH:4]=2)=[N:14][CH:15]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:17]=1

Participants

7

Reactant 4

HCID 90073-MethoxyphenolHCID 11430Potassium CarbonateHCID 24758Sodium hydride2×HCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridine

Product 1

HCID 199860193-Chloro-2-p-methoxyphenoxy-5-trifluoromethylpyridine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

P-Methoxyphenol (1.5 g) was added to a suspension of sodium hydride (0.6 g 50% oil dispersion, washed with petroleum) in dry dimethyl sulphoxide (30 ml) and the mixture stirred for 15 minutes. A solution of the combined products (1.5 g) from several preparations carried out as described in paragraph (d), in dimethylsulphoxide (20 ml) was added to the reaction mixture and heated to 60° C. for four hours. A further amount of sodium hydride (0.3 g of 50% oil dispersion, washed with petroleum), and potassium carbonate (1.38 g) was added. Heating was continued for another 4 hours. The mixture was poured into ice and water, and extracted with ether (400 ml). The ether extracts were washed with water, dilute sodium hydroxide, and water, dried, and evaporated to give the product.

Workup

  1. additionwas added to the reaction mixture
  2. temperatureHeating
  3. waitwas continued for another 4 hours
  4. extractionextracted with ether (400 ml)
  5. washThe ether extracts were washed with water, dilute sodium hydroxide, and water
  6. customdried
  7. customevaporated
  8. customto give the product

Sources & evidence

ORD record
ord-691e331fb5bf4b1aa81f024fcbef8df3
Source dataset
uspto-grants-1990_05
Patent number
US04925947

Reaction notes

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