Hydrochloric Acid → HCID 18972968, compound

HRID 2394308Notes

Reaction equation

HRID 2394308 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10]Br)[CH:5]=[CH:6][C:7]=1[Cl:8].[Mg].[C:13](OCC)(=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15].Cl>CCOCC.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:13](=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 5462224MagnesiumHCID 151493894-(2-Bromoethyl)-1,2-dichlorobenzene

Product 1

HCID 18972968HCID 18972968, compoundYield 12.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(3,4-Dichlorophenyl)ethyl bromide (5 g, 19.7 mmol) was added slowly to a suspension of magnesium turnings (0.48 g, 19.7 mmol) in ether (30 ml). After spontaneous reflux had finished the mixture was stirred under reflux for 15 minutes and allowed to cool to room temperature. The mixture was added dropwise via cannula to a stirred, cooled (-25° C.) solution of diethyl oxalate (3 g, 20.7 mmol) in THF (15 ml). The mixture was stirred at -10° C. for 30 minutes and allowed to warm to room temperature. Hydrochloric acid (2M, 15 ml) was added and the mixture was extracted with ether (2×20 ml). The combined organic fractions were washed with water, dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate/hexane (10:90) to give the title compound (0.7 g).

Workup

  1. temperatureAfter spontaneous reflux
  2. temperatureunder reflux for 15 minutes
  3. additionThe mixture was added dropwise via cannula to a stirred
  4. stirringThe mixture was stirred at -10° C. for 30 minutes
  5. temperatureto warm to room temperature
  6. extractionthe mixture was extracted with ether (2×20 ml)
  7. washThe combined organic fractions were washed with water
  8. dry with materialdried (Na2SO4)
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by column chromatography on silica gel
  11. washeluting with ethyl acetate/hexane (10:90)

Sources & evidence

ORD record
ord-e21e29ca666c4f359173d5616f43645f
Source dataset
uspto-grants-1998_09
Patent number
US05811431

Reaction notes

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