Ethyl 2-bromopropionate → HCID 15016293, compound

HRID 2106612Notes

Reaction equation

HRID 2106612 reaction equation
[Na].[F:2][C:3]1[CH:4]=[C:5]([N:9]2[CH:13]=[N:12][C:11]([OH:14])=[N:10]2)[CH:6]=[CH:7][CH:8]=1.Br[CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(O)C.CS(C)=O>[CH2:20]([O:19][C:17]([CH:16]([O:14][C:11]1[N:12]=[CH:13][N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([F:2])[CH:4]=2)[N:10]=1)[CH3:22])=[O:18])[CH3:21]

Participants

6

Reactant 3

HCID 79040Ethyl 2-bromopropionateHCID 5360545SodiumHCID 178517996HCID 178517996, compound

Product 1

HCID 15016293HCID 15016293, compoundYield 32.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

A 1.7 g portion of sodium was dissolved in 50 ml of absolute ethanol, and that solution was added to a solution of 13.3 g of 1-(3-fluorophenyl)-3-hydroxy-1,2,4-1H-triazole in 150 ml of dimethylsulfoxide. The solution was heated on the steam bath for 15 minutes, and then 13.5 g of ethyl 2-bromopropionate was added and the mixture was held on the steam bath for 2 hours. It was then poured over ice-water, and the aqueous mixture was extracted with diethyl ether. The organic layer was washed with water and with brine, and was then dried with sodium sulfate and phase separation paper. The solvent was removed under vacuum, and the product was recrystallized from aqueous ethanol to obtain 6.7 g of the desired product, m.p. 35°-37°.

Workup

  1. temperatureThe solution was heated on the steam bath for 15 minutes
  2. extractionthe aqueous mixture was extracted with diethyl ether
  3. washThe organic layer was washed with water and with brine
  4. dry with materialwas then dried with sodium sulfate and phase separation paper
  5. customThe solvent was removed under vacuum
  6. customthe product was recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-eaa1913c03744accbf1ffa1e33686d20
Source dataset
uspto-grants-1990_06
Patent number
US04931083

Reaction notes

Loading…