Methyl iodide → 4-Bromo-2-fluoro-benzoic acid methyl ester

HRID 1397498Notes

Reaction equation

HRID 1397498 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1.IC.[C:14](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:14])=[O:7])=[C:4]([F:11])[CH:3]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 3026814-Bromo-2-fluorobenzoic acid

Product 1

HCID 113453114-Bromo-2-fluoro-benzoic acid methyl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

An ambient suspension of 4-bromo-2-fluorobenzoic acid (15.0 g, 68.5 mmol), iodomethane (21.0 mL, 342.5 mmol), and potassium carbonate (19.0 g, 137 mmol) in N,N-dimethylformamide (200 mL) was stirred at room temperature for 16 h, after which it was diluted with ethyl acetate (200 mL) and water (100 mL). The layers were separated, and the organics were washed with water (3×100 mL) and brine (1×100 mL), dried over sodium sulfate, and concentrated under reduced pressure. The residue was passed through a plug of SiO2 gel, eluting with 50% ethyl acetate in hexane, to give the title compound as a solid. MS (ESI) m/z 233 [M+H]+.

Workup

  1. customThe layers were separated
  2. washthe organics were washed with water (3×100 mL) and brine (1×100 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washeluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-68232a0fcc6545919d567fc91135ea14
Source dataset
uspto-grants-2014_12
Patent number
US08901152B2

Reaction notes

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