Methanol → HCID 67244456, compound

Temperature

0 °C

A dried 25 ml of two-neck round bottom flask was filled with argon gas. The solution of 4-amino-2-chloro-5-iodo-benzonitrile (63.8 mg, 0.23 mmol) in tetrahydrofuran was put into the flask and cooled to 0° C. To the solution was added Borane-THF complex (2 eq, 0.46 mmol, 0.4 ml) slowly. The temperature of the mixture was raised and heated to reflux for 12 hours. After confirming the completion of the reaction with TLC, to the solution was added methanol slowly (generation of bubbles) and stirred for 2 hours. The methanol was removed under reduced pressure and the residue was extracted with ethylacetate. The ethylacetate layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to yield a yellow syrup (46.5 mg, 71.85%).

1. additionA dried 25 ml of two-neck round bottom flask was filled with argon gas
2. additionTo the solution was added Borane-THF complex (2 eq, 0.46 mmol, 0.4 ml) slowly
3. temperatureThe temperature of the mixture was raised
4. temperatureheated
5. temperatureto reflux for 12 hours
6. customthe completion of the reaction with TLC
7. customThe methanol was removed under reduced pressure
8. extractionthe residue was extracted with ethylacetate
9. washThe ethylacetate layer was washed with water and brine
10. dry with materialdried over Na2SO4
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure

ORD record

ord-f15079f6c0cb46a18487142d38c36829

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07960584B2