Methyl iodide → 2,3-Difluorotoluene

HRID 2260905Notes

Reaction equation

HRID 2260905 reaction equation
[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[CH:6][C:7]=1[F:8].[Mg].[CH3:11]I.[Cl-].[NH4+]>O1CCCC1.[Cu]I>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:11]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 676754-Bromo-1,2-difluorobenzeneHCID 5462224Magnesium

Product 1

HCID 27742282,3-Difluorotoluene

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, 82.5 g of 3,4-difluorobromobenzene (1) dissolved in 150 mL of tetrahydrofuran (THF) was added dropwise to 12.5 g of dried magnesium, and after completing the dropwise addition, the mixture was refluxed for 1 hour. The resulting solution was added dropwise to 15 mL of THF having 91.5 g of methyl iodide and 12.3 g of copper(I) iodide added thereto under cooling with an ice bath. After stirring over night, a saturated ammonium chloride aqueous solution was added thereto to terminate the reaction. The aqueous layer was extracted with diethyl ether, which was added to the organic layer, and the organic layer was washed with a saturated saline and then dried over anhydrous magnesium sulfate. The organic layer was distilled to obtain 37.6 g of 2,3-difluorotoluene (2)

Workup

  1. additionthe dropwise addition
  2. temperaturethe mixture was refluxed for 1 hour
  3. additionadded
  4. temperatureunder cooling with an ice bath
  5. customto terminate
  6. customthe reaction
  7. extractionThe aqueous layer was extracted with diethyl ether, which
  8. additionwas added to the organic layer
  9. washthe organic layer was washed with a saturated saline
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationThe organic layer was distilled

Sources & evidence

ORD record
ord-f4b7e765bc3d465eb36be7b62ce67372
Source dataset
uspto-grants-2010_12
Patent number
US07846513B2

Reaction notes

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