Water → Methyl 5-nitro-2-(2,6-dimethoxyphenyl)-benzoate

HRID 1358111Notes

Reaction equation

HRID 1358111 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1B(O)O.[N+:14]([C:17]1[CH:18]=[CH:19][C:20](Br)=[C:21]([CH:26]=1)[C:22]([O:24][CH3:25])=[O:23])([O-:16])=[O:15].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N+:14]([C:17]1[CH:18]=[CH:19][C:20]([C:4]2[C:3]([O:2][CH3:1])=[CH:8][CH:7]=[CH:6][C:5]=2[O:9][CH3:10])=[C:21]([CH:26]=1)[C:22]([O:24][CH3:25])=[O:23])([O-:16])=[O:15]

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 245494Methyl 2-Bromo-5-nitrobenzoateHCID 2734343(2,6-Dimethoxyphenyl)boronic acid

Product 1

HCID 11001627Methyl 5-nitro-2-(2,6-dimethoxyphenyl)-benzoate

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of Example 1A, methyl 5-nitro-2-bromobenzoate (25.8 g, 99.2 mmol), (21.7 g, 119 mmol), cesium carbonate (97.1 g, 298 mmol), and dichlorobis(triphenylphosphine)palladium(II) (3.5 g, 5.0 mmol) in DMF (300 mL) was stirred for 24 hours at 80° C., cooled to 23° C., treated with water (600 mL), and extracted with ethyl acetate. The extract was dried (Na2SO4), filtered, and concentrated, during which a light yellow solid precipitated. The mixture was placed in a freezer (−20° C.) for 2 hours and filtered to provide the desired compound. MS (DCI/NH3) m/z 318 (M+H)+ and 335 (M+NH4)+.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated, during which a light yellow solid
  5. customprecipitated
  6. filtrationfiltered

Sources & evidence

ORD record
ord-5f5b5da28a724e21959d6bd0983c4888
Source dataset
uspto-grants-2003_07
Patent number
US06593480B2

Reaction notes

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