Cesium carbonate → Methyl 3-(4-methylphenyl)-5-nitrobenzoate

HRID 2278716Notes

Reaction equation

HRID 2278716 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].B(O)(O)[C:16]1[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:22][C:19]1[CH:20]=[CH:21][C:16]([C:2]2[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=2)=[CH:17][CH:18]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 79799Tolylboronic acidHCID 7020599Methyl 3-iodo-5-nitrobenzoate

Product 1

HCID 57851213Methyl 3-(4-methylphenyl)-5-nitrobenzoate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a stirred solution of methyl 3-iodo-5-nitrobenzoate (7.76 g, 24 mmol) and p-tolylboronic acid (3.94 g, 28 mmol) in toluene (576 mL) was added cesium carbonate (9.4 g, 28 mmol) in water (7.8 mL). The mixture was purged with nitrogen, and then tetrakis(triphenylphosphine)palladium(0) (860 mg, 0.74 mmol) was added at room temperature. The reaction mixture was heated to reflux for 3 days. After cooling, the mixture was filtered through Celite and the filtrate was concentrated. The residue was purified by flash chromatography to afford a white solid.

Workup

  1. customThe mixture was purged with nitrogen
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 3 days
  4. temperatureAfter cooling
  5. filtrationthe mixture was filtered through Celite
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by flash chromatography
  8. customto afford a white solid

Sources & evidence

ORD record
ord-e774cae0887640d285d2a4ee2211b4f2
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

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