Sodium Carbonate → 1-(3-Methoxyphenyl)-2-methyl-4-nitrobenzene

HRID 1700993Notes

Reaction equation

HRID 1700993 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].[CH3:12][O:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(O)C.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>[CH3:12][O:13][C:14]1[CH:19]=[C:18]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=2[CH3:11])[CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2516721-Bromo-2-methyl-4-nitrobenzeneHCID 2734370(3-Methoxyphenyl)boronic acid

Product 1

HCID 183192671-(3-Methoxyphenyl)-2-methyl-4-nitrobenzeneYield 90.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 2-bromo-5-nitrotoluene (40.0 gm, 185 mmol) in 1,2-dimethoxyethane (600 mL) was added to tetrakis(triphenylphosphine)palladium(0) (9.77 gm, 9.25 mmol) under nitrogen at room temperature. A solution of 3-methoxyphenylboronic acid (31.5 gm, 207 mmol) in ethanol (150 mL) was added. Finally, 2M aqueous sodium carbonate (800 mL) was added and the mixture was heated under reflux with rapid mechanical stirring for 18 h. After being cooled, the mixture was partitioned between ethyl acetate and water and the organic phase was dried (Na2SO4) and concentrated under reduced pressure. Purification by column chromatography on silica gel eluting with hexane:ethyl acetate=98:2 then 95:5 gave 1-(3-methoxyphenyl)-2-methyl-4-nitrobenzene (40.55 gm, 90%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux with rapid
  3. temperatureAfter being cooled
  4. customthe mixture was partitioned between ethyl acetate and water
  5. dry with materialthe organic phase was dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography on silica gel eluting with hexane

Sources & evidence

ORD record
ord-fc0c661dc72c4bb9ab3fab391cb08d6c
Source dataset
uspto-grants-2002_02
Patent number
US06350907B1

Reaction notes

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