Réaction #69111

Équation de réaction

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

bromine

sodium thiosulfate

→

product

Rendement 89.1%

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

Rendement 89.1%

Solvants

DCM

bicarbonate

DCM

DCM

Conditions de réaction

Traitement

1. 1
   workup.WAITAfter an hour at room temperature
2. 2
   AutreThe organic layer was separated
3. 3
   Lavagefurther washed with the 50:50 aqueous mixture
4. 4
   Séchagedried over magnesium sulfate
5. 5
   Autreevaporated
6. 6
   AutreThe crude yellow solid was triturated with diethyl ether and solid
7. 7
   Autreisolated
8. 8
   Autredried

Mode opératoire

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)

Source