Dimethylformamide → Methyl 5-bromo-3-chloro-2-methoxybenzoate

HRID 2373785Notes

Reaction equation

HRID 2373785 reaction equation
[CH3:1]I.[Br:3][C:4]1[CH:5]=[C:6]([Cl:14])[C:7](O)=[C:8]([CH:12]=1)C(O)=O.[C:15]([O-:18])([O-])=[O:16].[Cs+].[Cs+].CN([CH:24]=[O:25])C>CCOC(C)=O>[CH3:1][O:18][C:15](=[O:16])[C:8]1[CH:12]=[C:4]([Br:3])[CH:5]=[C:6]([Cl:14])[C:7]=1[O:25][CH3:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 2244665-Bromo-3-chloro-2-hydroxybenzoic acid

Product 1

HCID 11346502Methyl 5-bromo-3-chloro-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Methyl Iodide (3.83 g, 27.04 mmol) was added to a solution of 5-Bromo-3-chloro-2-hydroxy-benzoic acid (1.7 g, 6.76 mmol) and Cs2CO3 (4.83 g, 14.86 mmol) in DMF (10 mL) and heated at 50° C. for 12 h. The reaction mixture was diluted with EtOAc (30 mL) and filtered over celite pad. Filtrate was washed with water, brine and dried over Na2SO4. Solvent was removed and the residue was purified by silicagel column chromagography to get pure 5-Bromo-3-chloro-2-methoxy-benzoic acid methyl ester (1.56 g)

Workup

  1. filtrationfiltered over celite pad
  2. washFiltrate was washed with water, brine
  3. dry with materialdried over Na2SO4
  4. customSolvent was removed
  5. customthe residue was purified by silicagel column chromagography

Sources & evidence

ORD record
ord-9b6dc47cca714aa6800210a4c72c0c27
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Reaction notes

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