تفاعل #347792

معادلة التفاعل

1-Bromo-1-chloro-2,2,2-trifluorethane

senecialdehyde

sodium t-butoxide

→

5-bromo-5-chloro-4-hydroxy-2-methyl-6,6,6-trifluorohex-2-ene

المردود 73.8%

المذيبات

Tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe mixture was stirred at -60° C. for a further 30 minutes
2. 2
   أخرىOn completion of reaction
3. 3
   أخرىthe mass was quenched by controlled addition of saturated ammonium chloride solution (120 ml)
4. 4
   workup.ADDITIONHexane (500 ml) was added to the mixture
5. 5
   أخرىthe aqueous phase was separated
6. 6
   استخلاصextracted with further hexane (2×500 ml)
7. 7
   غسيلThe combined organics were washed with brine (2×100 ml)
8. 8
   أخرىDrying
9. 9
   تركيز(sodium sulphate) and concentration in vacuo

الإجراء التجريبي

Tetrahydrofuran (230 ml) and sodium t-butoxide (57.6 g; 40% w/v solution in dimethylformamide) was charged to a split-neck reaction flask, and cooled to -60° C. with stirring. 1-Bromo-1-chloro-2,2,2-trifluorethane (47.6 g) and senecialdehyde (20.9 g) were charged simultaneously over 25 minutes, then the mixture was stirred at -60° C. for a further 30 minutes. On completion of reaction, the mass was quenched by controlled addition of saturated ammonium chloride solution (120 ml). Hexane (500 ml) was added to the mixture, then the aqueous phase was separated and extracted with further hexane (2×500 ml). The combined organics were washed with brine (2×100 ml) and then water (3×20 ml). Drying (sodium sulphate) and concentration in vacuo then gave the product 5-bromo-5-chloro-4-hydroxy-2-methyl-6,6,6-trifluorohex-2-ene as a mobile yellow oil (50.1 g, 70% yield).

المصدر