1,2-Dibromoethane → HCID 68183475, compound

HRID 513697Notes

Reaction equation

HRID 513697 reaction equation
[Mg].BrCCBr.Br[C:7]1[CH:8]=[CH:9][C:10]([F:18])=[C:11]([CH:13]2[O:17][CH2:16][CH2:15][O:14]2)[CH:12]=1.[N+:19]([C:22]1[C:23]([CH:32]=[O:33])=[CH:24][CH:25]=[C:26]2[C:31]=1[N:30]=[CH:29][CH:28]=[CH:27]2)([O-:21])=[O:20]>C1COCC1>[O:14]1[CH2:15][CH2:16][O:17][CH:13]1[C:11]1[CH:12]=[C:7]([CH:32]([C:23]2[C:22]([N+:19]([O-:21])=[O:20])=[C:31]3[C:26]([CH:27]=[CH:28][CH:29]=[N:30]3)=[CH:25][CH:24]=2)[OH:33])[CH:8]=[CH:9][C:10]=1[F:18]

Participants

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 5462224MagnesiumHCID 117695548-Nitro-7-quinolinecarboxaldehydeHCID 184555852-(5-Bromo-2-fluorophenyl)-1,3-dioxolane

Product 1

HCID 68183475HCID 68183475, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Magnesium (983 mg, 40.5 mmol) was suspended in anhydrous THF (30 ml). 1,2-dibromoethane (0.17 ml, 2.02 mmol) was added and the solution was stirred at room temperature for 20 min. 2-(5-bromo-2-fluoro-phenyl)-[1,3]dioxolane 417 (3.2 g, 12.95 mmol) was added dropwise and the mixture was heated at 40° C. for 2 h. The mixture was allowed to cool to room temperature. The Grignard reagent (0.43M; 28.6 ml) was added to a suspension of 8-nitroquinoline-7-carbaldehyde 204 (2.5 g, 12.4 mmol) in dry THF (30 ml) at 0° C. under a nitrogen atmosphere. The mixture was stirred at room temperature for 30 min. The mixture was quenched with sat. NH4Cl (10 ml) and the aqueous phase was extracted with EtOAc (20 ml). The organic phase was washed with brine (10 ml), dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with heptane/EtOAc (50:50) as the eluent to give the title compound (3.39 g, 74%).

Workup

  1. temperaturethe mixture was heated at 40° C. for 2 h
  2. temperatureto cool to room temperature
  3. stirringThe mixture was stirred at room temperature for 30 min
  4. customThe mixture was quenched with sat. NH4Cl (10 ml)
  5. extractionthe aqueous phase was extracted with EtOAc (20 ml)
  6. washThe organic phase was washed with brine (10 ml)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by column chromatography with heptane/EtOAc (50:50) as the eluent

Sources & evidence

ORD record
ord-6dadb1431f37459f8b87789e4d0ac191
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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