Nitroethane → Benzoic acid, 4-(1-nitroethyl)-, methyl ester

HRID 923457Notes

Reaction equation

HRID 923457 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[N+:12]([CH2:15][CH3:16])([O-:14])=[O:13].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1C)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[NH4+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].COCCOC>[N+:12]([CH:15]([C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1)[CH3:16])([O-:14])=[O:13]

Participants

8

Reactant 5

HCID 6587NitroethaneHCID 10796Cesium carbonateHCID 12081Methyl 4-bromobenzoateHCID 25517Ammonium ChlorideHCID 27349372-(Di-tert-butylphosphino)-2'-methyl-1,1'-biphenyl

Product 1

HCID 11310314Benzoic acid, 4-(1-nitroethyl)-, methyl ester

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2.0 g of methyl 4-bromobenzoate, 1.3 ml of nitroethane, 172 mg of tris(dibenzylideneacetone)dipalladium(0), 232 mg of 2-(di-tert-butylphosphino)-2′-methylbiphenyl, 3.33 g of cesium carbonate, and 44 ml of 1,2-dimethoxyethane (DME) was stirred at 60° C. for 18 hours. The reaction mixture was left to be cooled to room temperature, followed by adding a saturated aqueous ammonium chloride solution and extracting with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 1.44 g of methyl 4-(1-nitroethyl)benzoate.

Workup

  1. waitThe reaction mixture was left
  2. temperatureto be cooled to room temperature
  3. extractionextracting with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was then evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d26483e44c7f4261b2c5d8cf803a75f9
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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