تفاعل #6995
ord-fa247d297f624cf2b98f0abe5ea5ce3a
معادلة التفاعل
المتفاعلات
ظروف التفاعل
المعالجة
- 1أخرىUnder N2 in a round-bottomed flask fitted with a reflux condenser and magnetic stirrer
- 2أخرىaccording to the method in Collection of Czechoslovakian Chemical Communications, 1975, vol. 40, p728)
- 3workup.ADDITIONwere added
- 4درجة الحرارةthe mixture was heated
- 5درجة الحرارةto reflux overnight
- 6غسيلeluting with CHCl3:CH3OH:AcOH (9:1:0.5)
- 7أخرىthe reaction
- 8استخلاصre-extracted with additional EtOAc
- 9غسيلwashed with H2O and saturated NaCl
- 10تجفيفdried over MgSO4
- 11أخرىRemoval of the solvent in vacuo
- 12أخرىgave a dark brown colored oil, 2.6 g
الإجراء التجريبي
Under N2 in a round-bottomed flask fitted with a reflux condenser and magnetic stirrer were placed 6.37 g (19.55 mmol) of cesium carbonate and 3.2 g (19.55 mmol) of 3,4-dichlorophenol (both from Aldrich Chem. Co., Milwaukee, Wis.) in 60 mL of anhydrous toluene. After stirring the mixture for 5 min., 89 mg (0.24 mmol) of copper (II) trifluoromethanesulfonate (copper triflate) and 0.26g (9.78 mmol) of 5-fluoro-2-iodobenzoic acid (prepared according to the method in Collection of Czechoslovakian Chemical Communications, 1975, vol. 40, p728) were added and the mixture was heated to reflux overnight. Progress of the reaction was monitored using thin layer chromatography (tic), eluting with CHCl3:CH3OH:AcOH (9:1:0.5). After allowing the reaction to cool to room temperature, the mixture was diluted with water and EtOAc; the aqueous layer was acidified with 6 N HCl and re-extracted with additional EtOAc. The organic layers were combined, washed with H2O and saturated NaCl and dried over MgSO4. Removal of the solvent in vacuo gave a dark brown colored oil, 2.6 g, as a mixture of title product and unreacted 5-fluoro-2-iodobenzoic acid.