تفاعل #159481

معادلة التفاعل

3-Bromo-4′-chloro-4-ethylbiphenyl

6,6-dimethylbicyclo[3.1.1]heptane-2,4-dione

potassium phosphate

→

3-(4′-chloro-4-ethylbiphen-3-yl)-6,6-dimethylbicyclo[3.1.1]heptane-2,4-dione

المذيبات

ethyl acetate

1,2-dimethoxyethane

ظروف التفاعل

المعالجة

1. 1
   أخرىprepared by the method of W
2. 2
   درجة الحرارةThe mixture is cooled to room temperature
3. 3
   غسيلwashed with 2 M aqueous hydrochloric acid
4. 4
   غسيلThe organic phase is washed with brine
5. 5
   تجفيفdried over anhydrous magnesium sulfate
6. 6
   ترشيحfiltered
7. 7
   أخرىthe filtrate is evaporated under reduced pressure
8. 8
   أخرىpurified by preparative reverse-phase HPLC

الإجراء التجريبي

3-Bromo-4′-chloro-4-ethylbiphenyl (0.200 g, 0.68 mmol) is added to a mixture of 6,6-dimethylbicyclo[3.1.1]heptane-2,4-dione (0.124 g, 0.81 mmol), prepared by the method of W. Childers et al., US2006/0004108, powdered potassium phosphate (0.316 g, 1.49 mmol), palladium (II) acetate (0.008 g, 0.034 mmol) and (2-dicyclohexylphosphino)-2′,4′,6′-triisopropylbiphenyl (0.024 g, 0.051 mmol) in degassed 1,2-dimethoxyethane (2 ml) and the mixture is stirred and heated to 160° C. for 1 hour under microwave irradiation. The mixture is cooled to room temperature, diluted with ethyl acetate and washed with 2 M aqueous hydrochloric acid. The organic phase is washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is taken up in N,N-dimethylformamide (2 ml) and purified by preparative reverse-phase HPLC to give 3-(4′-chloro-4-ethylbiphen-3-yl)-6,6-dimethylbicyclo[3.1.1]heptane-2,4-dione.

المصدر