반응 #69111

반응 방정식

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

bromine

sodium thiosulfate

→

product

수율 89.1%

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

수율 89.1%

용매

DCM

bicarbonate

DCM

DCM

반응 조건

후처리

1. 1
   workup.WAITAfter an hour at room temperature
2. 2
   기타The organic layer was separated
3. 3
   세척further washed with the 50:50 aqueous mixture
4. 4
   건조dried over magnesium sulfate
5. 5
   기타evaporated
6. 6
   기타The crude yellow solid was triturated with diethyl ether and solid
7. 7
   기타isolated
8. 8
   기타dried

실험 절차

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)

출처