Sodium Carbonate → Methyl 4-formyl-2-methoxybenzoate

HRID 2102910Notes

Reaction equation

HRID 2102910 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.[CH:14]([O-])=[O:15].[Na+].C([O-])([O-])=O.[Na+].[Na+]>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.CN(C=O)C>[CH:14]([C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1)=[O:15]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2723810Sodium FormateHCID 15128242Methyl 4-bromo-2-methoxybenzoate

Product 1

HCID 18510332Methyl 4-formyl-2-methoxybenzoate

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A slow stream of CO was passed into a suspension of methyl 4-bromo-2-methoxybenzoate (2.4 g, 0.010 mol), bis(triphenylphosphine)palladium(II) chloride (140 mg, 0.00020 mol), sodium formate (1.02 g, 0.0150 mol), and dry DMF (10 mL). The mixture was vigorously stirred at 110° C. for 2 h. After cooling, the mixture was treated with aqueous Na2CO3 solution and extracted with EtOAc. The extract was washed with brine, dried (Na2SO4), and concentrated. The residue was purified by column chromatography on silica gel with AcOEt-hexane as eluent (0 to 50%) to give a colorless oil.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with EtOAc
  3. washThe extract was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel with AcOEt-hexane as eluent (0 to 50%)
  7. customto give a colorless oil

Sources & evidence

ORD record
ord-ab9e98d904e343e999df0b0c6b57151a
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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