تفاعل #2304293

ord-2f9392ae39e84e32ae39be28ded178ed

معادلة التفاعل

Brc1ccc(OCc2ccccc2)cc1
4-benzyloxybromobenzene
OB(O)c1ccc(OC(F)(F)F)cc1
4-(trifluoromethoxy)benzeneboronic acid
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
COCCOC
ethylene glycol dimethyl ether
FC(F)(F)Oc1ccc(-c2ccc(OCc3ccccc3)cc2)cc1
4-benzyloxy-4′-(trifluoromethoxy)biphenyl
المردود 35.9%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    استخلاصThe reaction mixture was extracted with toluene
  2. 2
    تجفيفthe organic layer was dried with anhydrous magnesium sulfate
  3. 3
    أخرىThe solvent was evaporated away
  4. 4
    أخرىthe resulting residue was purified through silica gel chromatography (elution solvent: heptane/toluene=7/3)
  5. 5
    أخرىrecrystallized from heptane

الإجراء التجريبي

A reaction mixture comprising 6.7 g of 4-benzyloxybromobenzene, 5.0 g of 4-(trifluoromethoxy)benzeneboronic acid, 0.3 g of tetrakis(triphenylphosphine)palladium(0), 5.1 g of sodium carbonate, 100 ml of ethylene glycol dimethyl ether and 20 ml of pure water was refluxed for 5 hours. The reaction mixture was extracted with toluene, and the organic layer was dried with anhydrous magnesium sulfate. The solvent was evaporated away, and the resulting residue was purified through silica gel chromatography (elution solvent: heptane/toluene=7/3) and recrystallized from heptane, and 3.0 g of 4-benzyloxy-4′-(trifluoromethoxy)biphenyl was obtained. m.p.: 136-137.2° C.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07407691B2uspto-grants-2008_08