Methyl iodide → Methyl 3-bromo-2-fluorobenzoate

HRID 2370647Notes

Reaction equation

HRID 2370647 reaction equation
[Br:1][C:2]1[C:3]([F:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].I[CH3:13]>CN(C)C=O.O.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([F:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:13])=[O:6]

Participants

6

Reactant 2

HCID 6328Methyl iodideHCID 27363133-Bromo-2-fluorobenzoic acid

Product 1

HCID 21584505Methyl 3-bromo-2-fluorobenzoate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-bromo-2-fluorobenzoic acid (10 g, 0.045 mol) in N,N-dimethylformamide (50 mL) was added iodomethane (5 mL) dropwise. The reaction was heated to 50° C. for 24 hours. After the reaction was cooled and diluted with water (500 mL), ethyl acetate (200 mL) was added. The organic phase was separated, dried over MgSO4, filtered, and concentrated to provide the title compound.

Workup

  1. temperatureAfter the reaction was cooled
  2. additionwas added
  3. customThe organic phase was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-004b4cba9f2445258012f860f23e5978
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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