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

HRID 2366461Notes

Reaction equation

HRID 2366461 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.[Na+]>CN(C=O)C>[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

5

Reactant 3

HCID 6328Methyl iodideHCID 3026814-Bromo-2-fluorobenzoic acidHCID 516892Sodium Bicarbonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-2-fluorobenzoic acid (30.8 g) in DMF (150 mL) was added iodomethane (17.5 mL) and powdered sodium hydrogencarbonate (23.5 g). The mixture was stirred for 18 hours and partitioned between ethyl acetate and brine. The organic phase was isolated, washed with dilute sodium bisulfite solution and brine and concentrated. The concentrate was flash chromatographed on silica gel with 7-20% ethyl acetate/hexanes.

Workup

  1. custompartitioned between ethyl acetate and brine
  2. customThe organic phase was isolated
  3. washwashed with dilute sodium bisulfite solution and brine
  4. concentrationconcentrated
  5. customchromatographed on silica gel with 7-20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-7c1eba1c78a34a3ab3d17cf475f32f5f
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

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