تفاعل #69111

معادلة التفاعل

5-trifluoromethyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine

bromine

sodium thiosulfate

→

product

المردود 89.1%

3-Bromo-5-Trifluoromethyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine

المردود 89.1%

المذيبات

DCM

bicarbonate

DCM

DCM

ظروف التفاعل

المعالجة

1. 1
   workup.WAITAfter an hour at room temperature
2. 2
   أخرىThe organic layer was separated
3. 3
   غسيلfurther washed with the 50:50 aqueous mixture
4. 4
   تجفيفdried over magnesium sulfate
5. 5
   أخرىevaporated
6. 6
   أخرىThe crude yellow solid was triturated with diethyl ether and solid
7. 7
   أخرىisolated
8. 8
   أخرىdried

الإجراء التجريبي

To a stirred solution of 5-trifluoromethyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine (53.7 g, 158 mmol) in DCM (250 mL) was added a solution of bromine (16 mL, 316 mmol) in DCM (50 mL) dropwise. No significant exotherm was observed. After an hour at room temperature, the reaction mixture had thickened and stirring ceased. The reaction was deemed complete by tlc and was diluted with 1.2 litres of DCM and 50:50 saturated bicarbonate: saturated sodium thiosulfate aqueous solution. The organic layer was separated and further washed with the 50:50 aqueous mixture, dried over magnesium sulfate and evaporated. The crude yellow solid was triturated with diethyl ether and solid isolated and dried to give the product as a yellow powder (59 g, 59% yield)

المصدر