Isovaleryl chloride → HCID 59834381, compound

HRID 230153Notes

Reaction equation

HRID 230153 reaction equation
Br[C:2]1[C:3]([O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[F:25])=[N:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])=[N:6][CH:7]=1.C([Mg]Cl)(C)C.[C:31](Cl)(=[O:36])[CH2:32][CH:33]([CH3:35])[CH3:34]>C1COCC1>[F:16][C:10]1[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=1[O:8][C:5]1[N:4]=[C:3]([O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[F:25])[C:2]([C:31](=[O:36])[CH2:32][CH:33]([CH3:35])[CH3:34])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 66054Isovaleryl chlorideHCID 59834408HCID 59834408, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 59834381HCID 59834381, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

5-Bromo-2,4-bis-(2,4-difluoro-phenoxy)-pyrimidine (0.5 g, 1.2 mmol) was dissolved in 25 mL THF and cooled to 0° C. Isopropyl magnesium chloride (0.8 mL, 1.44 mmol) was added, and the reaction mixture was stirred for an hour at 0° C. Isovaleryl chloride (1.47 mL, 12.0 mmol) was then added, and the reaction mixture was stirred for another hour at 0° C. The reaction was quenched with 35 mL of saturated aqueous sodium bicarbonate and 25 mL water. The aqueous mixture was extracted three times with 25 mL EtOAc, and the combined organic layers were washed with saturated aqueous brine, dried (Na2SO4), filtered, and evaporated under reduced pressure. The residue was eluted through silica gel using 20% EtOAc in hexanes to yield 0.429 g (85%) of 1-[2,4-bis-(2,4-difluoro-phenoxy)-pyrimidin-5-yl]-3-methyl-butan-1-one. Mass Spec. M+H=421.

Workup

  1. stirringthe reaction mixture was stirred for another hour at 0° C
  2. customThe reaction was quenched with 35 mL of saturated aqueous sodium bicarbonate and 25 mL water
  3. extractionThe aqueous mixture was extracted three times with 25 mL EtOAc
  4. washthe combined organic layers were washed with saturated aqueous brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. washThe residue was eluted through silica gel using 20% EtOAc in hexanes

Sources & evidence

ORD record
ord-47b8e70b374d49e39bbb54c6308eddb1
Source dataset
uspto-grants-2009_07
Patent number
US07566708B2

Reaction notes

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