Reaction #2348098

Reaction equation

compound ( 10 )

2,3-difluoro-4-ethoxy-6-methylphenylboric acid

hydrogen peroxide

sodium

→

2,3-difluoro-5-methylphenol

Solvents

THF

Conditions

Workup

1. 1
   TemperatureUnder cooling with an ice bath
2. 2
   TemperatureUnder cooling with an ice bath
3. 3
   Otherto terminate
4. 4
   Otherthe reaction
5. 5
   Extractionan aqueous layer was extracted with diethyl ether, which
6. 6
   workup.ADDITIONwas added to the organic layer
7. 7
   WashThe organic layer was washed with a saturated sodium hydrogensufite aqueous solution and saturated saline
8. 8
   Dryingdried over anhydrous magnesium sulfate
9. 9
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure

Procedure

Under cooling with an ice bath, 6.57 g of aqueous hydrogen peroxide was slowly added dropwise to the compound (10) having been dissolved in 37 mL of THF, followed by stirring at room temperature for 3 hours. Under cooling with an ice bath, 20 mL of a saturated sodium hydrogensufite aqueous solution was added thereto to terminate the reaction, and an aqueous layer was extracted with diethyl ether, which was added to the organic layer. The organic layer was washed with a saturated sodium hydrogensufite aqueous solution and saturated saline, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 3.84 g of 2,3-difluoro-5-methylphenol (11).

Source