反応 #69111

反応方程式

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

bromine

sodium thiosulfate

→

product

収率 89.1%

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

収率 89.1%

溶媒

DCM

bicarbonate

DCM

DCM

反応条件

後処理

1. 1
   workup.WAITAfter an hour at room temperature
2. 2
   その他The organic layer was separated
3. 3
   洗浄further washed with the 50:50 aqueous mixture
4. 4
   乾燥dried over magnesium sulfate
5. 5
   その他evaporated
6. 6
   その他The crude yellow solid was triturated with diethyl ether and solid
7. 7
   その他isolated
8. 8
   その他dried

実験手順

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)

出典