Sodium Carbonate → Methyl 2-chloro-4-formylbenzoate

HRID 2102934Notes

Reaction equation

HRID 2102934 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([Cl:12])[CH:3]=1.[CH:13]([O-])=[O:14].[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>[Cl:12][C:4]1[CH:3]=[C:2]([CH:13]=[O:14])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2723810Sodium FormateHCID 22058730Methyl 4-Bromo-2-chlorobenzoate

Product 1

HCID 57461225Methyl 2-chloro-4-formylbenzoate

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-chlorobenzoate (1.50 g, 0.00601 mol), bis(triphenylphosphine)palladium(II) chloride (80 mg, 0.0001 mol), sodium formate (613 mg, 0.00902 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 chromatographed on silica gel with AcOEt-hexane to give the product as a colorless oil (becomes a white solid when stored in a refrigerator).

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 chromatographed on silica gel with AcOEt-hexane

Sources & evidence

ORD record
ord-4f8cfcd247a04ce0bbb7a632fb7f9690
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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