HCID 57758592, compound → HCID 57758588, compound

HRID 229408Notes

Reaction equation

HRID 229408 reaction equation
[F:1][C:2]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:3]=1[O:4][C:5]1[N:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])[C:8]([CH:20]([C:22]2[CH:27]=[C:26]([S:28][CH3:29])[CH:25]=[CH:24][C:23]=2[CH3:30])[OH:21])=[CH:7][N:6]=1>C(Cl)Cl.O=[Mn]=O>[F:1][C:2]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:3]=1[O:4][C:5]1[N:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])[C:8]([C:20]([C:22]2[CH:27]=[C:26]([S:28][CH3:29])[CH:25]=[CH:24][C:23]=2[CH3:30])=[O:21])=[CH:7][N:6]=1

Participants

4

Reactant 1

HCID 57758592HCID 57758592, compound

Product 1

HCID 57758588HCID 57758588, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

[2,4-Bis-(2,4-difluoro-phenoxy)-pyrimidin-5-yl]-(2-methyl-5-methylsulfanyl-phenyl)-methanol (2.15 g, 4.281 mmol) was dissolved in 40 mL methylene chloride together with 10.0 g of MnO2, and the reaction mixture was heated to reflux for 16 hours. The reaction mixture was cooled and filtered through Celite. The filtrate was concentrated under reduced pressure, and the resulting residue was recrystallized from methylene chloride/hexanes to yield 1.816 g of [2,4-Bis-(2,4-difluoro-phenoxy)-pyrimidin-5-yl]-(2-methyl-5-methylsulfanyl-phenyl)-methanone, MS (M+H)=501.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 16 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered through Celite
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was recrystallized from methylene chloride/hexanes

Sources & evidence

ORD record
ord-d954ac2a099b4716a5d9133afe372f94
Source dataset
uspto-grants-2009_07
Patent number
US07563799B2

Reaction notes

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