Nitromethane → HCID 57590089, compound

HRID 1925005Notes

Reaction equation

HRID 1925005 reaction equation
[N+:1]([CH3:4])([O-:3])=[O:2].[H-].[Na+].[O-]S([O-])(=O)=O.[Mg+2].[CH3:13][O:14][C:15](=[O:25])[C:16]1[C:21]([F:22])=[CH:20][C:19]([Br:23])=[CH:18][C:17]=1F>CS(C)=O>[CH3:13][O:14][C:15](=[O:25])[C:16]1[C:17]([CH2:4][N+:1]([O-:3])=[O:2])=[CH:18][C:19]([Br:23])=[CH:20][C:21]=1[F:22]

Participants

6

Reactant 4

HCID 6375NitromethaneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 24758Sodium hydrideHCID 26343953Methyl 4-bromo-2,6-difluorobenzoate

Product 1

HCID 57590089HCID 57590089, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Nitromethane (10 mL, 169 mmol, 8 equiv.) is added cautiously to a suspension of sodium hydride (4.05 g, 169 mmol, 8 equiv.) and MgSO4 (40 g) in DMSO (100 mL) at rt and the resulting slurry is stirred for 0.25 h. To the resulting yellow slurry is added 4-bromo-2,6-difluorobenzoic acid methyl ester (5.3 g, 21 mmol) and the mixture is stirred at rt for 3 days at which point all the starting material has been consumed. Water (200 mL) and 6M HCl (50 mL) is added followed by DCM (200 mL). More water (500 mL) is added to yield a clear biphasic system. The aqueous layer is extracted with DCM (3×100 mL), the DCM layers are then combined, washed with saturated NaHCO3 and brine, and dried over MgSO4. Evaporation of the solvent affords an orange solid containing 64% of the desired material, used without further purification. LCMS; Rt=1.27 min (64%).

Workup

  1. stirringthe mixture is stirred at rt for 3 days at which point all the starting material
  2. customhas been consumed
  3. additionWater (200 mL) and 6M HCl (50 mL) is added
  4. additionMore water (500 mL) is added
  5. customto yield a clear biphasic system
  6. extractionThe aqueous layer is extracted with DCM (3×100 mL)
  7. washwashed with saturated NaHCO3 and brine
  8. dry with materialdried over MgSO4
  9. customEvaporation of the solvent
  10. customaffords an orange solid
  11. customused without further purification

Sources & evidence

ORD record
ord-168b34d3ca414da9a78f66d046e2bf8b
Source dataset
uspto-grants-2012_05
Patent number
US08178530B2

Reaction notes

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