Reaction #2348087

Reaction equation

ammonium chloride

methyl iodide

magnesium

3,4-difluorobromobenzene

→

2,3-difluorotoluene

Solvents

THF

tetrahydrofuran

Conditions

Workup

1. 1
   workup.ADDITIONthe dropwise addition
2. 2
   Temperaturethe mixture was refluxed for 1 hour
3. 3
   workup.ADDITIONadded
4. 4
   Temperatureunder cooling with an ice bath
5. 5
   Otherto terminate
6. 6
   Otherthe reaction
7. 7
   ExtractionThe aqueous layer was extracted with diethyl ether, which
8. 8
   workup.ADDITIONwas added to the organic layer
9. 9
   Washthe organic layer was washed with a saturated saline
10. 10
    Dryingdried over anhydrous magnesium sulfate
11. 11
    workup.DISTILLATIONThe organic layer was distilled

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)

Source