Iodine → 2,4-Dichloro-6-(4-methoxyphenyl)(1,3,5)triazine

HRID 618604Notes

Reaction equation

HRID 618604 reaction equation
[Mg].II.Br[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.[N:13]1[C:20]([Cl:21])=[N:19][C:17](Cl)=[N:16][C:14]=1[Cl:15]>O1CCCC1>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:17]2[N:19]=[C:20]([Cl:21])[N:13]=[C:14]([Cl:15])[N:16]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 807IodineHCID 77304-BromoanisoleHCID 7954Cyanuric chlorideHCID 5462224Magnesium

Product 1

HCID 110105692,4-Dichloro-6-(4-methoxyphenyl)(1,3,5)triazineYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
60 °C

Procedure

Grignard reaction: In a 500 ml sulfonating flask having a stirrer, dropping funnel, condenser and internal thermometer, 7.3 g (0.3 mol) of magnesium turnings and a few grains of iodine are initially introduced into 60 ml of dry tetrahydrofuran (THF). Under dry protective gas (nitrogen), 56.1 g (0.3 mol) of 4-bromoanisole, dissolved in 100 ml of THF, are slowly added dropwise at 60° C. After the complete dissolution of the Mg turnings, the mixture is stirred at 60° C. for 90 minutes. The Grignard solution is then added dropwise at 5° C. under nitrogen in the course of 60 minutes to a solution of 55.3 g (0.3 mol) of cyanuric chloride in 150 ml of THF. The mixture is evaporated to dryness at room temperature, 500 ml of dil. hydrochloric acid are allowed to run in and the mixture is extracted with 300 ml of methylene chloride. For working-up, the solvent is removed in vacuo, and the semisolid residue is tritrated with a little isopropanol and filtered off with suction. Purification is carried out by recrystallization from toluene/hexane (1:1). 62.8 g (82% of theory) of 6-(4-methoxyphenyl)-2,4-dichloro-1,3,5-triazine are obtained (m.p.: 131-134° C.).

Workup

  1. customGrignard reaction
  2. additionare slowly added dropwise at 60° C
  3. customThe mixture is evaporated to dryness at room temperature
  4. extractionis extracted with 300 ml of methylene chloride
  5. customthe solvent is removed in vacuo
  6. filtrationfiltered off with suction
  7. customPurification
  8. customis carried out by recrystallization from toluene/hexane (1:1)

Sources & evidence

ORD record
ord-384e036c5b714bf396bcf1a8b7304b36
Source dataset
uspto-grants-1999_09
Patent number
US05955060

Reaction notes

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