Dimethylformamide → Methyl 3-bromo-2-chlorobenzoate

HRID 658107Notes

Reaction equation

HRID 658107 reaction equation
CN([CH:4]=[O:5])C.[Br:6][C:7]1[C:8]([Cl:16])=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10](O)=[O:11].CI.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[Br:6][C:7]1[C:8]([Cl:16])=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([O:5][CH3:4])=[O:11]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 331243-bromo-2-chlorobenzoic acid

Product 1

HCID 67516858Methyl 3-bromo-2-chlorobenzoateYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a DMF solution (30 ml) containing 2.70 g of 3-bromo-2-chlorobenzoic acid were added 1.10 ml of methyl iodide and 2.38 g of potassium carbonate in order at room temperature, followed by 1 hour of stirring. The reaction liquid was mixed with water and then diluted with ethyl acetate. After a layer separation operation, the organic layer was washed with water and saturated brine in that order, dried with anhydrous magnesium sulfate and then concentrated under a reduced pressure. The thus obtained residue was purified by a silica gel column chromatography using ethyl acetate-n-hexane (100:3) as the elution solvent to obtain 2.26 g (79%) of methyl 3-bromo-2-chlorobenzoate. FA: 250

Workup

  1. customThe reaction liquid
  2. customAfter a layer separation operation
  3. washthe organic layer was washed with water and saturated brine in that order
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. customThe thus obtained residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-ebc5c54746d348e7b0e61ed8d2e09cac
Source dataset
uspto-grants-2011_12
Patent number
US08076367B2

Reaction notes

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