Indole → 3-iodo-1H-indole

Into a 500 mL 3-necked round bottom flask, was placed a solution of 1H-indole (10 g, 85.40 mmol) in MeOH/H2O (150/30 mL). To this was added potassium iodide (15.6 g, 93.98 mmol). To the mixture was added sodium hydroxide (3.76 g, 94.00 mmol). To the above was added 12 (23.88 g, 94.02 mmol) in several batches. The resulting solution was allowed to react, with stirring, for 3 hours while the temperature was maintained at room temperature. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:10). The reaction mixture was then quenched by the adding 100 mL of H2O. A filtration was performed. The filter cake was washed 3 times with 200 mL of water. This resulted in 18 g (84%) of 3-iodo-1H-indole as a light yellow solid.

1. customInto a 500 mL 3-necked round bottom flask, was placed
2. customto react
3. customThe reaction mixture was then quenched by the adding 100 mL of H2O
4. filtrationA filtration
5. washThe filter cake was washed 3 times with 200 mL of water
6. customThis resulted in 18 g (84%) of 3-iodo-1H-indole as a light yellow solid

ORD record

ord-8bd8bfb8bda54ecea98a0238d14a9ae6

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07696229B2