3,4-Dichlorophenol → HCID 13102700, compound

HRID 1758001Notes

Reaction equation

HRID 1758001 reaction equation
CC([O-])(C)C.[K+].[Cl:7][C:8]1[CH:9]=[C:10]([OH:15])[CH:11]=[CH:12][C:13]=1[Cl:14].Cl[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][N:18]=1>CS(C)=O>[Cl:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][C:13]=1[Cl:14])[O:15][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][N:18]=1

Participants

5

Reactant 3

HCID 72583,4-DichlorophenolHCID 783082-Chloro-5-nitropyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 13102700HCID 13102700, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
90 °C

Procedure

To 44.9 g of t-BuOK in 250 ml of DMSO was added 65.2 g of 3,4-dichlorophenol in 50 ml of DMSO causing a temperature rise to between 65°-70° C. To this warm solution was added 2-chloro-5-nitropyridine (63.4 g) which raised the temperature to 90° C. The mixture was stirred without heating until the temperature dropped to 40° C. (~1 hr). The reaction mixture was poured into 1 kilogram (kg) of ice-water and the solid collected by filtration. The solid was dissolved in CH2Cl2, dried over Na2CO3, treated with charcoal, redried over MgSO4 and then filtered. The CH2Cl2 solution was concentrated to 250 ml, then diluted to 700 ml with hexane and allowed to stand overnight. From this solution, a crystalline material was collected by filtration and 94.8 g of 2-(3,4-dichlorophenoxy)-5-nitropyridine obtained, m.p. 101°-102.5° C.

Workup

  1. temperaturewithout heating until the temperature
  2. additiondropped to 40° C. (~1 hr)
  3. filtrationthe solid collected by filtration
  4. dissolutionThe solid was dissolved in CH2Cl2
  5. dry with materialdried over Na2CO3
  6. additiontreated with charcoal
  7. dry with materialredried over MgSO4
  8. filtrationfiltered
  9. concentrationThe CH2Cl2 solution was concentrated to 250 ml
  10. additiondiluted to 700 ml with hexane
  11. filtrationFrom this solution, a crystalline material was collected by filtration and 94.8 g of 2-(3,4-dichlorophenoxy)-5-nitropyridine
  12. customobtained

Sources & evidence

ORD record
ord-308ec0f5b5c546869db26c66fa55864d
Source dataset
uspto-grants-1983_02
Patent number
US04371537

Reaction notes

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