2,6-Dichlorophenol → HCID 22398418, compound

HRID 1530869Notes

Reaction equation

HRID 1530869 reaction equation
[OH-].[K+].C(O)C.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=1[OH:14].[Cl:15][C:16]1[N:21]=[C:20](Cl)[CH:19]=[C:18]([Cl:23])[N:17]=1>O1CCCC1>[Cl:15][C:16]1[N:17]=[C:18]([Cl:23])[CH:19]=[C:20]([O:14][C:8]2[C:7]([Cl:6])=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:13])[N:21]=1

Participants

5

Reactant 3

HCID 68992,6-DichlorophenolHCID 773782,4,6-TrichloropyrimidineHCID 21946426Potassium hydroxide ethanol

Product 1

HCID 22398418HCID 22398418, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium hydroxide/ethanol (10%; 0.035 mol) was added to a solution of 2,6-dichlorophenol (0.035 mol) in tetrahydrofuran (100 ml). The mixture was stirred and 2,4,6-trichloropyrimidine (0.044 mol) was added. The mixture was stirred overnight at 60° C. The reaction was quenched with NaOH 1N solution. The aqueous layers were extracted with EtOAc several times and then the organic layers were combined and washed with NaOH 3N and saturated NaCl, dried and concentrated. The residue was recrystallized from CH2Cl2/hexane. The precipitate was filtered off and dried, yielding 5.98 g 2,4-dichloro-6-(2,6-dichlorophenoxy)pyrimidine (55%) (interm. 12).

Workup

  1. stirringThe mixture was stirred overnight at 60° C
  2. customThe reaction was quenched with NaOH 1N solution
  3. extractionThe aqueous layers were extracted with EtOAc several times
  4. washwashed with NaOH 3N and saturated NaCl
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was recrystallized from CH2Cl2/hexane
  8. filtrationThe precipitate was filtered off
  9. customdried

Sources & evidence

ORD record
ord-19840bfb8dba4f1d8a5168949f738bc2
Source dataset
uspto-grants-2001_03
Patent number
US06197779B1

Reaction notes

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