Ethyl 2-bromopropionate → HCID 14392491, compound

HRID 1382148Notes

Reaction equation

HRID 1382148 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:10]1[C:14](=[O:15])[N:13]([CH:16]([F:18])[F:17])[C:12]([CH3:19])=[N:11]1.Br[CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23]>CN(C)C=O.C(OCC)C>[Br:8][C:6]1[CH:7]=[C:2]([Br:1])[C:3]([N:10]2[C:14](=[O:15])[N:13]([CH:16]([F:17])[F:18])[C:12]([CH3:19])=[N:11]2)=[CH:4][C:5]=1[O:9][CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

5

Reactant 2

HCID 79040Ethyl 2-bromopropionateHCID 13961780HCID 13961780, compound

Product 1

HCID 14392491HCID 14392491, compoundYield 64.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1.25 g (0.0031 mole) of 1-(2,4-dibromo-5-hydroxyphenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one in 60 mL of N,N-dimethylformamide was added 0.57 g (0.0033 mole) of ethyl 2-bromopropionate. The resultant mixture was heated at 130° . for two hours, then was cooled. The solvent was evaporated from the mixture under reduced pressure, leaving a solid. This solid was dissolved in diethyl ether, and the solution was washed first with water, then with an aqueous 10% sodium hydroxide solution. The organic solution was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 1.0 g of ethyl 2-[2,4-dibromo-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]propionate as an oil, Compound 8.

Workup

  1. temperaturewas cooled
  2. customThe solvent was evaporated from the mixture under reduced pressure
  3. customleaving a solid
  4. washthe solution was washed first with water
  5. dry with materialThe organic solution was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3048b0041c464772ae2fa9f4ba8bc73e
Source dataset
uspto-grants-1989_02
Patent number
US04806145

Reaction notes

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