Potassium Carbonate → HCID 14853654, compound

HRID 2073686Notes

Reaction equation

HRID 2073686 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:13](=[O:14])[N:12]([CH3:15])[C:11]([CH:16]([F:18])[F:17])=[N:10]2)=[C:4]([F:19])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:27]([CH3:35])[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([F:19])[C:5]([N:9]2[C:13](=[O:14])[N:12]([CH3:15])[C:11]([CH:16]([F:17])[F:18])=[N:10]2)=[CH:6][C:7]=1[O:8][CH:27]([CH3:35])[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 545327tert-Butyl 2-bromopropanoateHCID 148536531-(4-chloro-2-fluoro-5-hydroxyphenyl)-3-difluoromethyl-4,5-dihydro-4-methyl-1,2,4-triazol-5(1H)-one

Product 1

HCID 14853654HCID 14853654, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 0.7 g (0.0023 mole) of 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-3-difluoromethyl-4,5-dihydro-4-methyl-1,2,4-triazol-5(1H)-one, 0.9 g (0.0067 mole) of potassium carbonate, and 0.6 g (0.0027 mole) of tert-butyl 2-bromopropionate in 40 mL of acetone was stirred at room temperature for approximately 72 hours. The reaction mixture was partitioned between water and methylene chloride and the organic phase was washed with water. After drying over anhydrous magnesium sulfate the organic phase was filtered. Evaporation of the filtrate under reduced pressure yielded 0.9 g of tert-butyl 2-[2-chloro-4-fluoro-5-(3-difluoromethyl-4,5-dihydro-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]propionate as an oil, Compound 40.

Workup

  1. customThe reaction mixture was partitioned between water and methylene chloride
  2. washthe organic phase was washed with water
  3. dry with materialAfter drying over anhydrous magnesium sulfate the organic phase
  4. filtrationwas filtered
  5. customEvaporation of the filtrate under reduced pressure

Sources & evidence

ORD record
ord-d8b45adc0e43454e88396c2dbbec0bd2
Source dataset
uspto-grants-1990_04
Patent number
US04919708

Reaction notes

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