Réaction #2348098

ord-7613853d66ba438eadd12cc4f30dce05

Équation de réaction

CCOc1cc(C)c(OB(O)O)c(F)c1F
compound ( 10 )
CCOc1cc(C)c(OB(O)O)c(F)c1F
2,3-difluoro-4-ethoxy-6-methylphenylboric acid
OO
hydrogen peroxide
[Na]
sodium
Cc1cc(O)c(F)c(F)c1
2,3-difluoro-5-methylphenol

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

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

Mode opératoire

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

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07846513B2uspto-grants-2010_12