تفاعل #172157

معادلة التفاعل

triethylamine

1-adamantanemethanol

bromodifluoroacetyl chloride

→

bromodifluoroacetic acid adamantane-1-ylmethyl ester

المردود 95.0%

المذيبات

diethyl ether

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwere added
2. 2
   workup.ADDITIONby adding
3. 3
   workup.WAITThis reaction solution was left
4. 4
   workup.STIRRINGwhile stirring, until it
5. 5
   أخرىreached room temperature
6. 6
   workup.STIRRINGThe reaction solution was further stirred for 1 hour at room temperature
7. 7
   غسيلSubsequently, the reaction solution was washed with 5 kg of water
8. 8
   غسيلThe thus-obtained organic layer was washed with 5 kg of saturated sodium hydrogencarbonate solution, with 5 kg of saturated sodium chloride solution
9. 9
   تجفيفThe washed organic layer was dried with magnesium sulfate
10. 10
    workup.DISTILLATIONsubjected to solvent distillation

الإجراء التجريبي

Into a 50-L reaction vessel, 476 g (3.18 mol, 1.11 eq) of 1-adamantanemethanol and 5.5 kg of diethyl ether were added. The resulting solution was suspended by stirring, followed by adding thereto 615 g (2.86 mol, 1.0 eq) of bromodifluoroacetyl chloride. The suspended solution was cooled down to 0° C. Then, 578 g (5.72 mol, 2.0 eq) of triethylamine was slowly dropped to the cooled suspended solution. This reaction solution was left, while stirring, until it reached room temperature. The reaction solution was further stirred for 1 hour at room temperature. Subsequently, the reaction solution was washed with 5 kg of water. The thus-obtained organic layer was washed with 5 kg of saturated sodium hydrogencarbonate solution, with 5 kg of saturated sodium chloride solution, and then, with 5 kg of water. The washed organic layer was dried with magnesium sulfate and subjected to solvent distillation. With this, 878 g of target bromodifluoroacetic acid adamantane-1-ylmethyl ester was obtained (yield: 95%, purity: 100%).

المصدر