Methyl iodide → Methyl 2-bromo-6-fluorobenzoate

HRID 1476807Notes

Reaction equation

HRID 1476807 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([OH:6])=[O:5].[C:12](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O.O>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([O:6][CH3:12])=[O:5]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 3026212-Bromo-6-fluorobenzoic acid

Product 1

HCID 12192163Methyl 2-bromo-6-fluorobenzoateYield 99.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution 2-bromo-6-fluorobenzoic acid (50 g, 0.229 mol) and potassium carbonate (31.6 g, 0.229 mol) in N,N-dimethylformamide (250 mL) was added dropwise methyl iodide (51.83 g, 0.365 mol) over a 30 minute period. The reaction mixture was stirred at RT for 3.5 hours. The resulting mixture was diluted with water (500 mL) and extracted with EtOAc (3×300 mL). The combined organic layers were washed with 1M aqueous HCl (100 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give the title compound (53 g, 99.7%).

Workup

  1. extractionextracted with EtOAc (3×300 mL)
  2. washThe combined organic layers were washed with 1M aqueous HCl (100 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2030783fae6241b7b9b1aa6f642e320c
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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