tert-Butyl methyl ether → HCID 21254021, compound

HRID 1531442Notes

Reaction equation

HRID 1531442 reaction equation
[B-](F)(F)(F)F.[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+]([F:21])(CC2)C1.[Cl:22][C:23]1[CH:28]=[C:27]([Cl:29])[C:26]([CH3:30])=[CH:25][C:24]=1[C:31]1[CH:35]=[C:34]([O:36][CH:37]([F:39])[F:38])[N:33]([CH3:40])[N:32]=1.C(OC)(C)(C)C>C(#N)C>[Cl:22][C:23]1[CH:28]=[C:27]([Cl:29])[C:26]([CH3:30])=[CH:25][C:24]=1[C:31]1[C:35]([F:21])=[C:34]([O:36][CH:37]([F:38])[F:39])[N:33]([CH3:40])[N:32]=1

Participants

5

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 2724933Selectfluor2×HCID 15672343HCID 15672343, compound

Product 1

HCID 21254021HCID 21254021, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

46.3 g (131 mmol) of Selectfluor™ were added to a solution of 40.2 g (131 mmol) of 3-(2,4-dichloro-5-methylphenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole in 0.5 l of acetonitrile. After the mixture had been stirred for 12 hours at room temperature, it was heated for a further hour at reflux temperature. Thereafter, three batches of 6.9 g (20 mmol) of Selectfluor™ were added to the reaction mixture, a little at a time, and the mixture was heated in each case for one hour at reflux temperature. The resulting mixture was subsequently treated with 0.5 l of methyl tert-butyl ether. The organic phase was washed with water, saturated aqueous sodium hydrogen carbonate solution and again with water, then dried over magnesium sulfate and finally concentrated. The crude product was purified by means of silica gel chromatography (eluent:hexane/ethyl acetate=9:1). Yield: 20.3 g.

Workup

  1. temperatureit was heated for a further hour
  2. temperatureat reflux temperature
  3. temperaturea little at a time, and the mixture was heated in each case for one hour
  4. temperatureat reflux temperature
  5. washThe organic phase was washed with water, saturated aqueous sodium hydrogen carbonate solution and again with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationfinally concentrated
  8. customThe crude product was purified by means of silica gel chromatography (eluent:hexane/ethyl acetate=9:1)

Sources & evidence

ORD record
ord-f0208c4472c146ae9eb8696c50f8f60a
Source dataset
uspto-grants-2001_03
Patent number
US06197973B1

Reaction notes

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