تفاعل #68752

معادلة التفاعل

5-bromo-2-trifluoromethoxybenzaldehyde

boron trifluoride etherate

water

boron trifluoride etherate

1,2-bis(trimethylsiloxy)cyclobutene

→

2-(5-bromo-2-trifluoromethoxyphenyl)cyclopentane-1,3-dione

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGAfter stirring for 24 hours at room temperature the reaction mixture
2. 2
   أخرىis then quenched with saturated aqueous ammonium chloride solution (50 ml)
3. 3
   استخلاصextracted with dichloromethane (2×50 ml)
4. 4
   استخلاصThe crude product is extracted from the organic phase
5. 5
   غسيلby washing with 0.5 M aqueous potassium carbonate solution (×3)
6. 6
   استخلاصFinal extraction with dichloromethane (×3)
7. 7
   غسيلby washing with brine
8. 8
   تجفيفthen drying over magnesium sulfate and filtration
9. 9
   تركيزConcentration in vacuo
10. 10
    أخرىgives a crude product which
11. 11
    أخرىis purified by preparative reverse phase HPLC

الإجراء التجريبي

To a solution of 5-bromo-2-trifluoromethoxybenzaldehyde (2.0 g, 7.43 mmol) in anhydrous dichloromethane (40 ml) at room temperature is added boron trifluoride etherate (1.13 ml, 8.92 mmol) then 1,2-bis(trimethylsiloxy)cyclobutene (2.86 ml, 11.2 mmol). The mixture is stirred at room temperature for 23 hours, followed by addition of distilled water (1.2 ml) and additional boron trifluoride etherate (14.1 ml, 112 mmol). After stirring for 24 hours at room temperature the reaction mixture is then quenched with saturated aqueous ammonium chloride solution (50 ml) and extracted with dichloromethane (2×50 ml). The crude product is extracted from the organic phase by washing with 0.5 M aqueous potassium carbonate solution (×3), then acidified to pH 1 with concentrated hydrochloric acid. Final extraction with dichloromethane (×3) is followed by washing with brine then drying over magnesium sulfate and filtration. Concentration in vacuo gives a crude product which is purified by preparative reverse phase HPLC to afford 2-(5-bromo-2-trifluoromethoxyphenyl)cyclopentane-1,3-dione.

المصدر