Dimethylformamide → Benzoic acid, 5-chloro-2-iodo-, methyl ester

HRID 2401386Notes

Reaction equation

HRID 2401386 reaction equation
[C:1]([O-])(O)=O.[Na+].[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([I:16])=[C:11]([CH:15]=1)[C:12]([OH:14])=[O:13].CN(C=O)C.CI>O.CCOC(C)=O>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([I:16])=[C:11]([CH:15]=1)[C:12]([O:14][CH3:1])=[O:13]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 1394515-Chloro-2-iodobenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 23510379Benzoic acid, 5-chloro-2-iodo-, methyl esterYield 97.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a round bottomed flask was added NaHCO3 (22.31 g, 266 mmol), 5-chloro-2-iodobenzoic acid (25 g, 89 mmol), DMF, and MeI (11.07 mL, 177 mmol). The reaction was stirred at room temperature overnight. The reaction was diluted with water and EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water (3×) and brine before being dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage to afford the titled compound (25.81 g, 87 mmol). LC/MS m/z 297 [M+H]+.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organic layers were washed with water (3×) and brine
  4. dry with materialbefore being dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified via Biotage

Sources & evidence

ORD record
ord-9c7458ad579b4fc98218bab422c7e8e2
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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