Ethyl Acetate → Methyl 2-(2,4-dimethoxyphenyl)-5-nitrobenzoate

HRID 1968457Notes

Reaction equation

HRID 1968457 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1B(O)O.Br[C:15]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:16]=1[C:17]([O:19][CH3:20])=[O:18].C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CN(C)C=O.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C(OCC)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:15]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:16]=1[C:17]([O:19][CH3:20])=[O:18]

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 245494Methyl 2-Bromo-5-nitrobenzoateHCID 27343412,4-Dimethoxybenzeneboronic acid

Product 1

HCID 57990576Methyl 2-(2,4-dimethoxyphenyl)-5-nitrobenzoate

Reagents, catalysts & solvents 4

HCID 178419050HCID 178419050, compoundCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,4-dimethoxyphenylboronic acid (25.0 g, 137 mmol), methyl 2-bromo-5-nitrobenzoate (35.7 g, 137 mmol), cesium carbonate (89.4 g, 274 mmol) and bis(triphenylphosphine)palladium (II) dichloride (4.81 g, 6.85 mmol) was suspended in N, N-dimethylformamide (450 mL), and then stirred under argon atmosphere at 80° C. overnight. After cooling down, ethyl acetate (200 mL), diethylether (400 mL) and water (1000 mL) were added thereto, and then separated. The water layer was extracted with a mixed solvent of ethyl acetate (150 mL)-diethylether (150 mL) (twice). The organic layer was combined and washed with water (500 mL, 3 times) and saturated brine (500 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure to give the titled reference compound as a brown oil.

Workup

  1. temperatureAfter cooling down
  2. customseparated
  3. extractionThe water layer was extracted with a mixed solvent of ethyl acetate (150 mL)-diethylether (150 mL) (twice)
  4. washwashed with water (500 mL, 3 times) and saturated brine (500 mL) successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customto give the titled reference compound as a brown oil

Sources & evidence

ORD record
ord-a33a5b7b182d42388348cb8883de3910
Source dataset
uspto-grants-2013_04
Patent number
US08426406B2

Reaction notes

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