Methyl iodide → Methyl 3-bromo-2-fluorobenzoate

HRID 1175214Notes

Reaction equation

HRID 1175214 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].[C:12](=O)([O-])[O-].[K+].[K+].IC.CC(OC)(C)C>CN(C=O)C>[Br:1][C:2]1[C:3]([F:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:12])=[O:6]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 15413tert-Butyl methyl etherHCID 27363133-Bromo-2-fluorobenzoic acid

Product 1

HCID 21584505Methyl 3-bromo-2-fluorobenzoateYield 89.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 100 mL round bottom flask was added 3-bromo-2-fluorobenzoic acid (5.00 g, 22.8 mmol, Oakwood), potassium carbonate (3.17 g, 22.9 mmol), and DMF (30 mL). Iodomethane, 2 M in MTBE (11.6 ml, 23.2 mmol) was added and the reaction mixture was stirred at RT for 16 hours. The reaction was filtered and the filtrate concentrated was in vacuo. The resulting brown crude residue was taken up with EtOAc and again filtered and concentrated to give methyl 3-bromo-2-fluorobenzoate (4.76 g, 20.4 mmol, 89.5% yield), as a brown syrup that was used in the Step 2 without further purification.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate concentrated
  3. filtrationagain filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6f3bda2a993f464c88614095c260e517
Source dataset
uspto-grants-2010_11
Patent number
US07838676B2

Reaction notes

Loading…